Enantiopure

Distribution by Scientific Domains
Distribution within Chemistry

Terms modified by Enantiopure

  • enantiopure compound
  • enantiopure form

  • Selected Abstracts


    Regioselective Metal-Catalyzed Hydrophosphinylation of Alkynes: Synthesis of Enantiopure ,- or ,-Substituted Vinylphosphane Oxides

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 26 2009
    Amélie Duraud
    Abstract Palladium was found to catalyze regioselective Markovnikov addition of chiral enantiopure 1r -oxo-2c,5t -diphenylphospholane (1) to terminal alkynes, whereas rhodium catalysis offers selectively the (E)-anti-Markovnikov adduct. This strategy offers rapid access to chiral and enantiopure ,- or ,-substituted-1-alkenylphospholanes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Enantiopure (9-Anthryl)(2-piperidyl)- and (9-Anthryl)(2-pyridyl)methanols , Their Use as Chiral Modifiers for Heterogeneous Hydrogenation of Keto Esters over Pt/Al2O3

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 5 2007
    Arlette Solladié-Cavallo
    Abstract A route toward the synthesis of the erythro isomer of (9-anthryl)(2-piperidyl)methanol is presented as well as resolution and assignment of the structure (through NMR). The use of both the erythro and threo enantiopure isomers of this new amino alcohol, and its precursor [(9-anthryl)(2-pyridyl)methanol], as chiral modifiers for the Pt/Al2O3 hydrogenation of ethyl lactate showed that the erythro isomer is not necessarily the most efficient chiral modifier. This is probably because of the 9-anthryl group. The enantioselectivities that this compound provides are not, as one would expect, higher than those observed with the naphthyl group.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source]


    Complete Chiral Induction from Enantiopure 1,2-Diamines to Benzophenone-Based Achiral Bisphosphane Ligands in Noyori-Type RuII Catalysts

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 16 2006
    Qing Jing
    Abstract We report the design and synthesis of a novel class of RuII catalysts (3) composed of achiral benzophenone-based bisphosphane ligands and enantiopure 1,2-diamines for the asymmetric hydrogenation of aryl ketones. The developed catalysts show excellent enantioselectivities (up to 97,% ee) and activities (up to S/C = 10,000) in the hydrogenation of a variety of aromatic ketones.Complete chiral induction from the enantiopure 1,2-diamine to the achiral bisphosphane ligand was observed. The coordination of the C=O moiety in 3 to the cationic RuII center is considered to be of key importance in providing a higher thermodynamic and kinetic rotation barrier for the flexible bisphosphane ligand, resulting in the preferential formation of only one diastereomer, and thus explaining the high enantioselectivity of the catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]


    Synthesis of Enantiopure 1- r -Aryl-2- c,5- t -diphenylphospholane Oxides and Boranes by Pd-Catalyzed C,P Bond Formation

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 3 2006
    Martial Toffano
    Abstract New chiral enantiopure phospholane oxides 1 and boranes 5 were obtained from efficient carbon,phosphorus bond formation by organocuprate or palladium-catalyzed reactions. C,P cross-coupling reactions between chiral phosphane oxide 3 or borane 4 and various aryl derivatives are presented.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]


    Combining Designer Cells and Click Chemistry for a One-Pot Four-Step Preparation of Enantiopure ,-Hydroxytriazoles

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 13 2010
    Wiktor Szymanski
    Abstract The multistep catalytic process using designer cells, either added as freshly prepared suspensions or as stable lyophilized powder, and click reaction can be performed in one pot. The sequence of four reactions allows the production of both enantiomers of ,-hydroxytriazoles with high enantiomeric excess. [source]


    Enzymatic Synthesis of Enantiopure ,- and ,-Amino Acids by Phenylalanine Aminomutase-Catalysed Amination of Cinnamic Acid Derivatives

    CHEMBIOCHEM, Issue 2 2009
    Bian Wu
    Abstract The phenylalanine aminomutase (PAM) from Taxus chinensis catalyses the conversion of ,-phenylalanine to ,-phenylalanine, an important step in the biosynthesis of the N -benzoyl phenylisoserinoyl side-chain of the anticancer drug taxol. Mechanistic studies on PAM have suggested that (E)-cinnamic acid is an intermediate in the mutase reaction and that it can be released from the enzyme's active site. Here we describe a novel synthetic strategy that is based on the finding that ring-substituted (E)-cinnamic acids can serve as a substrate in PAM-catalysed ammonia addition reactions for the biocatalytic production of several important ,-amino acids. The enzyme has a broad substrate range and a high enantioselectivity with cinnamic acid derivatives; this allows the synthesis of several non-natural aromatic ,- and ,-amino acids in excellent enantiomeric excess (ee >99,%). The internal 5-methylene-3,5-dihydroimidazol-4-one (MIO) cofactor is essential for the PAM-catalysed amination reactions. The regioselectivity of amination reactions was influenced by the nature of the ring substituent. [source]


    ChemInform Abstract: Synthesis of Enantiopure 3,6,7,8-Tetrahydrochromeno[7,8-d]imidazoles via Asymmetric Ketone Hydrogenation in the Presence of RuCl2[Xyl-P-Phos][DAIPEN].

    CHEMINFORM, Issue 11 2009
    Andreas Marc Palmer
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    Enantioselective Scandium-Catalyzed Vinylsilane Additions: A New Approach to the Synthesis of Enantiopure ,,,-Unsaturated ,-Hydroxy Acid Derivatives.

    CHEMINFORM, Issue 1 2007
    David A. Evans
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]


    Stereoconservative Negishi Arylation and Alkynylation as an Efficient Approach to Enantiopure 2,2,-Diarylated 1,1,-Binaphthyls.

    CHEMINFORM, Issue 15 2005
    Katarina Krascsenicsova
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]


    ChemInform Abstract: Humicola lanuginosa Lipase Catalyzed Enantioselective Resolution of ,-Hydroxy Sulfides: Versatile Synthons for Enantiopure ,-Hydroxy Sulfoxides.

    CHEMINFORM, Issue 14 2002
    Satwinder Singh
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    ChemInform Abstract: Diastereoselective Electrophilic Fluorination of Enantiopure ,-Silylketones Using N-Fluoro-benzosulfonimide: Regio- and Enantioselective Synthesis of ,-Fluoroketones.

    CHEMINFORM, Issue 10 2002
    Dieter Enders
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    ChemInform Abstract: Palladium-Catalyzed Synthesis of Enantiopure 1,2,4,5-Tetrahydro-1,4-benzodiazepin-3-(3H)-one Derivatives.

    CHEMINFORM, Issue 39 2001
    Marta Catellani
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    ChemInform Abstract: Synthesis of Enantiopure N-Protected 4,5-Disubstituted 3-Pyrrolidinones and N-Protected 2,5-Disubstituted 3-Pyrrolidinones via the Dieckmann Reaction of Dicarbonyl Compounds Derived from Enantiopure ,-Amino Esters.

    CHEMINFORM, Issue 35 2001
    Yue Wang
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    ChemInform Abstract: Stereoselective Cyanation of Chiral ,-Amino Aldehydes by Reaction with Nagata,s Reagent: A Route to Enantiopure ,-Amino-,-hydroxy Acids.

    CHEMINFORM, Issue 31 2001
    Jose M. Andres
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    1-(,-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure ,-Aminophosphonic Acids

    CHEMISTRY - A EUROPEAN JOURNAL, Issue 27 2009
    Kirill
    Abstract Ooh Betti! A new diastereoselective synthesis of ,-aminophosphonates has been developed based on the reaction of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol (Betti base; see scheme, X=H, CH3, or Br). The reaction proceeds with high diastereoselectivity. Treatment with HCl results in the formation of the desired ,-aminophosphonic acids. A new diastereoselective synthesis of ,-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired ,-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl. [source]


    Highly Diastereoselective Diels,Alder Reactions with Enantiopure Sulfinyl-Substituted 1-Hydroxymethyldienes

    CHEMISTRY - A EUROPEAN JOURNAL, Issue 17 2005
    Roberto Fernández de la Pradilla Dr.
    Abstract Enantiopure hydroxy-2- and -3-sulfinyldienes undergo highly selective Diels,Alder cycloadditions with various dienophiles controlled by the chiral sulfur atom. The related hydroxy-2-sulfonyldienes display complementary ,-facial selectivity. [source]


    Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic Sevoflurane: A vibrational circular dichroism study

    CHIRALITY, Issue 8 2002
    Feng Wang
    Abstract 1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, compound B, is a product obtained in the degradation of the anesthetic Sevoflurane. Enantiopure (+)- B was investigated using vibrational circular dichroism (VCD). Experimental absorption and VCD spectra of (+)- B in CDCl3 solution in the 2,000,900 cm,1 region are compared with the ab initio predictions of absorption and VCD spectra obtained from density functional theory using B3LYP/6-31G* basis set for different conformers of (S)-1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane. This comparison indicates that (+)- B is of the (S)-configuration in CDCl3 solution, in agreement with previous literature results. Our results also indicate that this compound adopts six predominant conformations in CDCl3 solution. Chirality 14:618,624, 2002. © 2002 Wiley-Liss, Inc. [source]


    Water-Soluble Arene Ruthenium Complexes Containing a trans -1,2-Diaminocyclohexane Ligand as Enantioselective Transfer Hydrogenation Catalysts in Aqueous Solution

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, Issue 22 2005
    Jérôme Canivet
    Abstract The cationic chloro complexes [(arene)Ru(H2N,NH2)Cl]+ (1: arene = C6H6; 2: arene = p -MeC6H4iPr; 3: arene = C6Me6) have been synthesised from the corresponding arene ruthenium dichloride dimers and enantiopure (R,R or S,S) trans -1,2-diaminocyclohexane (H2N,NH2) and isolated as the chloride salts. The compounds are all water-soluble and, in the case of the hexamethylbenzene derivative 3, the aqua complex formed upon hydrolysis [(C6Me6)Ru(H2N,NH2)OH2]2+ (4) could be isolated as the tetrafluoroborate salt. The molecular structures of 3 and 4 have been determined by single-crystal X-ray diffraction analyses of [(C6Me6)Ru(H2N,NH2)Cl]Cl and [(C6Me6)Ru(H2N,NH2)OH2][BF4]2. Treatment of [Ru2(arene)2Cl4] with the monotosylated trans -1,2-diaminocyclohexane derivative (TsHN,NH2) does not yield the expected cationic complexes, analogous to 1,3 but the neutral deprotonated complexes [(arene)Ru(TsN,NH2)Cl] (5: arene = C6H6; 6: arene = p -MeC6H4iPr; 7: arene = C6Me6; 8: arene = C6H5COOMe). Hydrolysis of the chloro complex 7 in aqueous solution gave, upon precipitation of silver chloride, the corresponding monocationic aqua complex [(C6Me6)Ru(TsHN,NH2)(OH2)]+ (9) which was isolated and characterised as its tetrafluoroborate salt. The enantiopure complexes 1,9 have been employed as catalysts for the transfer hydrogenation of acetophenone in aqueous solution using sodium formate and water as a hydrogen source. The best results were obtained (60 °C) with 7, giving a catalytic turnover frequency of 43 h,1 and an enantiomeric excess of 93,%. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) [source]


    Asymmetric Total Synthesis of (+)-6- epi -Castanospermine by the Stereoselective Formation of a syn,anti Acetylenic 2-Amino-1,3-diol Stereotriad

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 15 2010
    Julien Louvel
    Abstract The asymmetric total synthesis of (+)-6- epi -castanospermine (1) is described herein. In this synthesis the diastereoselective addition of a racemic allenylzinc reagent to an enantiopure ,-alkoxy- tert -butylsulfinylimine is the key step and is followed by the formation of a piperidine ring by ring-closing metathesis and subsequent syn -dihydroxylation of an alkene. [source]


    Regioselective Metal-Catalyzed Hydrophosphinylation of Alkynes: Synthesis of Enantiopure ,- or ,-Substituted Vinylphosphane Oxides

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 26 2009
    Amélie Duraud
    Abstract Palladium was found to catalyze regioselective Markovnikov addition of chiral enantiopure 1r -oxo-2c,5t -diphenylphospholane (1) to terminal alkynes, whereas rhodium catalysis offers selectively the (E)-anti-Markovnikov adduct. This strategy offers rapid access to chiral and enantiopure ,- or ,-substituted-1-alkenylphospholanes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Enantiocomplementary Chemoenzymatic Asymmetric Synthesis of (R)- and (S)-Chromanemethanol

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 6 2009
    Michael Fuchs
    Abstract A non-lipase-based, enantiocomplementary chemoenzymatic route towards enantiopure (R)- and (S)-chromanemethanol (12), which are the key building blocks for the synthesis of stereoisomerically pure ,-tocopherols, has been achieved by the biocatalytic resolution of a racemic 2,2-disubstituted oxirane using an epoxide hydrolase and a halohydrin dehalogenase, which exhibit opposite enantiopreferences. The introduction of chirality at an early stage of the synthesis ensured a high efficiency, leading to total overall yields of 16 and 26,% for (R)- and (S)-chromanemethanol (12), respectively.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Stereoselective Synthesis of (2S,4R)-4-Hydroxypipecolic Acid

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 3 2008
    Ernesto G. Occhiato
    Abstract A new synthetic route to enantiopure (2S,4R)-4-hydroxypipecolic acid from commercial ethyl (3S)-4-chloro-3-hydroxybutanoate is reported. The synthesis is based on the Pd-catalyzed methoxycarbonylation of a 4-alkoxy-substituted ,-valerolactam-derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in 20,% yield over 10 steps. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]


    Complete Chiral Induction from Enantiopure 1,2-Diamines to Benzophenone-Based Achiral Bisphosphane Ligands in Noyori-Type RuII Catalysts

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 16 2006
    Qing Jing
    Abstract We report the design and synthesis of a novel class of RuII catalysts (3) composed of achiral benzophenone-based bisphosphane ligands and enantiopure 1,2-diamines for the asymmetric hydrogenation of aryl ketones. The developed catalysts show excellent enantioselectivities (up to 97,% ee) and activities (up to S/C = 10,000) in the hydrogenation of a variety of aromatic ketones.Complete chiral induction from the enantiopure 1,2-diamine to the achiral bisphosphane ligand was observed. The coordination of the C=O moiety in 3 to the cationic RuII center is considered to be of key importance in providing a higher thermodynamic and kinetic rotation barrier for the flexible bisphosphane ligand, resulting in the preferential formation of only one diastereomer, and thus explaining the high enantioselectivity of the catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]


    First Asymmetric Synthesis and Determination of the Absolute Configuration of a Lignan Isolated from Virola sebifera

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 10 2005
    Dieter Enders
    Abstract The first asymmetric synthesis of a lignan isolated from the seeds of Virola sebifera, one of the most widely spread Myristicaceae species in Brazil, in four steps (48,% overall yield) and with excellent stereoselectivity (de, ee , 96,%) is described. The key step is the asymmetric Michael addition of a lithiated enantiopure ,-amino nitrile to an enone, followed by ,-methylation and cleavage of the amino nitrile. The absolute configuration of the naturally occurring 1,4-diketone was determined by polarimetry as well as by CD spectroscopy and quantum chemical calculations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) [source]


    Synthesis of Enantiopure 1-Aryl-1-butylamines and 1-Aryl-3-butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)-Phenylglycine Amide

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 7 2004
    Jan Dalmolen
    Abstract The synthesis of enantiopure 1-aryl-1-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves: (a) formation of the chiral imines; (b) asymmetric addition of the allylzinc reagent; (c) removal of the chiral auxiliary by means of a reductive or non-reductive method. The reductive method provides 1-aryl-1-butylamines whereas the non-reductive method preserves the double bond to afford 1-aryl-3-butenylamines. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) [source]


    Asymmetric Synthesis of ,,,-Substituted ,-Sultones via Allylation of Chiral Lithiated Sulfonates

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 20 2003
    Dieter Enders
    Abstract The first auxiliary controlled asymmetric synthesis of enantiopure ,,,-substituted ,-sultones via ,-allylation of lithiated sulfonates by using 1,2:5,6-di- O -isopropylidene-,- D -allofuranose as chiral auxiliary is described. The high asymmetric inductions of the ,-allylations were reached in good to excellent yields. Successive epimerization-free cleavage of the auxiliary and diastereoselective ring closure of the sulfonic acid intermediates in a one-pot procedure led to the title compounds in good to excellent yields and diastereo- and enantiomeric excesses (de, ee , 98%). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]


    The Addition Reaction of Samarium Enolates and 2-Haloenolates Derived from Esters, and Amides to Imines.

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 17 2009
    4-Diamino Esters or Amides, Totally Stereoselective Synthesis of Enantiopure
    Abstract The addition reaction of samarium enolates and 2-haloenolates derived from esters and amides to imines takes place in an efficient manner. A novel protocol to perform the addition reaction of samarium enolates derived from esters or amides to chiral 2-aminoimines, with total stereoselectivity and without racemization, is also reported. The use of samarium enolates in place of other classic metallic enolates (lithium, magnesium, etc.) could be a valuable alternative to obtain enantiopure 3,4-diamino esters or amides, when enolates of low basicity are necessary. [source]


    The Use of Samarium Enolates, A Novel Alternative in the Addition Reactions to Imines.

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 9 2009
    4-Diamino Esters, Amides, Enantiopure , Synthesis of 3-Amino Esters
    Abstract An efficient reaction of tosylimines with a range of samarium enolates (derived from esters, and amides) is reported. The reaction with the ,-dibenzylamino- N - tert- butanesulfinimine derived from chiral phenylalaninal afforded the corresponding enantiopure 3,4-diamino ester with very high diastereoselectivity. [source]


    One-Pot, Regioselective Synthesis of Substituted Arylglycines for Kinetic Resolution by Penicillin G Acylase

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 11-12 2008
    Peter Grundmann
    Abstract Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an inexpensive route to a large variety of N -phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5,°C in acetic acid/HCl, this simple one-pot operation resulted in the formation of single regioisomers only (,98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH,8.0 occurred generally with E values>100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)- and (R)-antipodes of non-natural ,-amino acids in small- to large-scale quantities. [source]


    Fast and Enantioselective Production of 1-Aryl-1-propanols through a Single Pass, Continuous Flow Process

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 6 2008
    Miquel
    Abstract A functional polymer 4, obtained by reaction of (R)-2-(1-piperazinyl)-1,1,2-triphenylethanol with a Merrifield resin, has been loaded in a packed bed reactor and used as catalyst for the continuous enantioselective production of 1-arylpropanols by ethylation of aromatic aldehydes. The high catalytic activity depicted by 4 allows the complete conversion of the substrates with the use of stoichiometric reagent ratios and unprecedently short residence times (down to 2.8,min). In practice, a single-pass operation can be used for all the studied aldehydes, and productions of up to 13.0 mol/g,h are recorded. The sequential operation of the flow system for the uninterrupted synthesis of a small library of enantiopure 1-arylpropanols is also reported. [source]