Stereoselective Synthesis (stereoselective + synthesis)

Distribution by Scientific Domains
Distribution within Chemistry

Kinds of Stereoselective Synthesis

  • efficient stereoselective synthesis
  • facile stereoselective synthesis
  • highly stereoselective synthesis
  • novel stereoselective synthesis


  • Selected Abstracts


    Stereoselective Syntheses of the Octahydropyrano[2,3- b]pyridine DE Core of 'Upenamide via a Stannous Chloride-Induced Deacetalisation,Cyclisation Procedure

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 22 2007
    Cécilia Ménard-Moyon
    Abstract Two stereoselective syntheses of the octahydropyrano[2,3- b]pyridine DE hemiaminal core of the macrocyclic alkaloid 'upenamide are described. The syntheses proceeded through an efficient stannous chloride-induced deacetalisation,cyclisation procedure. The aza-annulation was stereoselective affording a single stereoisomer having the same relative configuration as in the natural product. The cis ring junction and the cis relationship between 2-H and 8a-H were established by NMR spectroscopy and confirmed by X-ray crystallography. An asymmetric synthesis of the octahydropyrano[2,3- b]pyridine ring system is also disclosed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source]


    Stereoselective Syntheses of (+)-,- (Ia) and (-)-,-Conhydrine (Ib) from L-Aspartic Acid.

    CHEMINFORM, Issue 40 2005
    Satyendra Kumar Pandey
    No abstract is available for this article. [source]


    Structure,Reactivity Relationships in Oxidative Carbon,Carbon Bond Forming Reactions: A Mild and Efficient Approach to Stereoselective Syntheses of 2,6-Disubstituted Tetrahydropyrones.

    CHEMINFORM, Issue 6 2005
    Lijun Wang
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]


    Construction of Terminal Conjugated Enynes: Regio- and Stereoselective Syntheses of 3-Alken-1-ynes and 1-Trimethylsilyl-3-alken-1-ynes from Alkenyldialkylboranes and (Trimethylsilyl)ethynyl Bromide.

    CHEMINFORM, Issue 44 2002
    Masayuki Hoshi
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]


    ChemInform Abstract: Palladium,Copper Catalyzed Synthesis of Benzofused Heterocycles with Two Heteroatoms: Novel and Highly Regio- and Stereoselective Syntheses of (E)-2-(2-Arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles and (E)-2-Alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzothiazines.

    CHEMINFORM, Issue 46 2001
    Nitya G. Kundu
    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 Syntheses of Allylic Amines Through Reduction of 1-Azadiene Intermediates.

    CHEMINFORM, Issue 7 2001
    Enrique Aguilar
    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]


    Stereoselective Synthesis of the First Chatt-Type Bis(dinitrogen)-Molybdenum(0) Complex with a Tetraphosphane Ligand

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, Issue 21 2008
    René Römer
    Abstract The first Chatt-type Mo0 dinitrogen complex with a tetraphosphane ligand has been prepared and characterized by NMR as well as infrared and Raman spectroscopy. Importantly, the employed reaction route allows the stereospecific synthesis of this complex as trans -[Mo(N2)2(meso -prP4)] (prP4 = a tetraphos ligand with a central propylene bridge). The stereoselectivity in the reaction course is induced by the oxido-iodido-molybdenum(IV) precursor [Mo(O)I(prP4)]+ which directs both phenyl groups of the bridging P atoms of prP4 into a meso configuration. The paper establishes a general strategy to synthesize mononuclear Mo0 dinitrogen and related molybdenum complexes with multidentate phosphane ligands which has not been possible to date. Moreover, the obtained molybdenum tetraphos N2 complex should exhibit a higher thermodynamic stability in the reactions of the Chatt cycle of synthetic nitrogen fixation than the conventional bis(diphos) complexes, due to the linkage of the two diphosphane units by an alkyl bridge. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]


    Stereoselective Synthesis of (2E,4Z)-Dienamides Employing (Triphenylphosphoranylidene)ketene

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 17 2009
    Steffen Pachali
    Abstract The three-component reaction between ylide Ph3PCCO, amines and aldehydes is known to afford selectively (E)-,,,-unsaturated amides. We applied a variant of this methodology to the preparation of (2E,4Z)-dienamides 11 utilizing the phosphonium salt formation from ethyl 5-aminopentanoate hydrochloride and Ph3PCCO followed by deprotonation with DBU and a Wittig olefination of the corresponding ylide with various (Z)-,,,-unsaturated aldehydes 10. The (2E,4Z)-dienamides 11 were isolated in yields of up to 80,%. The (Z)-configuration of the starting aldehydes 10 remained untouched during the reaction.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Stereoselective Synthesis of 2,6-Disubstituted-4-Aryltetrahydropyrans Using Sakurai,Hosomi,Prins,Friedel,Crafts Reaction

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 10 2009
    Udagandla C. Reddy
    Abstract The reaction of aldehydes with allyltrimethylsilane in arene solvents gives symmetrical 2,6-disubstituted-4-aryltetrahydropyrans in good yields. The reaction is highly stereoselective. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    First Stereoselective Synthesis of (1R,2R,4R)- and (1S,2R,4S)-2-Substituted-1-azabicyclo[2.2.1]heptanes

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 9 2009
    Pablo Etayo
    Abstract The first stereoselective synthesis of two diastereomeric 1-azabicyclo[2.2.1]heptanes substituted at the 2-position from an easily accessible (R)-2-substituted-4-piperidone is reported. The synthetic route involves the asymmetric one-carbon homologation of a chiral ketone followed by an intramolecular SN2-type cyclisation and led to target compounds in high overall yield by using a simple procedure in which purification of the intermediate compounds is not required. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Straightforward Strategy for the Stereoselective Synthesis of Spiro-Fused (C-5)Isoxazolino- or (C-3)Pyrazolino-(C-3)quinolin-2-ones from Baylis,Hillman Adducts by 1,3-Dipolar Cycloaddition and Reductive Cyclization,

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 32 2008
    Virender Singh
    Abstract A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis,Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives proceeded efficiently in the presence of In/HCl, whereas similar reductions of pyrazolines gave better yields when carried out in the presence of an Fe/AcOH mixture. However, similar attempts employing the Baylis,Hillman adduct of 2-nitrobenzaldehyde and methyl vinyl ketone did not yield the desired compounds.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]


    Stereoselective Synthesis of the Naturally Occurring 2-Pyranone Dodoneine

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 23 2008
    Paula Álvarez-Bercedo
    Abstract The first total synthesis of the naturally occurring dihydropyranone dodoneine is reported. Asymmetric allylation reactions were used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created by ring-closing metathesis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [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]


    Stereoselective Synthesis of 2-Deoxyglycosides from Sulfanyl Alkenes by Consecutive "One Pot" Cyclization and Glycosylation Reactions

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 15 2007
    Miguel A. Rodríguez
    Abstract 2-Deoxy-2-iodopyranosides 3, and 9,12 were synthesized from sulfanyl alkenes using a "one pot" consecutive cyclization,glycosylation process. Compared with the stepwise procedure, the "one pot" process gave significantly improved yields with similar or slightly lower selectivities. The "onepot" procedure was applied to the synthesis of 2,6-dideoxy-2-iodoglycoside 22, which was successfully deiodinated to afford the 2,6-dideoxyglycoside 23. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source]


    Utility of Azolium Triflates as Promoters for the Condensation of a Nucleoside Phosphoramidite and a Nucleoside in the Agrawal's Stereoselective Synthesis of Nucleoside Phosphorothioates,

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 24 2005
    Mamoru Hyodo
    Abstract This paper demonstrates that some azolium triflates, such as N -phenylimidazolium triflate, benzimidazolium triflate and N -methylbenzimidazolium triflate, are more useful than 1H -tetrazole as promoters for the stereoselective condensation of a 5,- O -free nucleoside and a stereochemically pure 5,- O -(p,p,-dimethoxytrityl)-3,- O -{(4R)-1H,3H -pyrrolo[1,2- c]-1,3,2-oxazaphospholidin}-2-yl 2,-deoxyribonucleoside (Rc- 1) or 5,- O -(p,p,-dimethoxytrityl)-3,- O -{(4S)-1H,3H -pyrrolo[1,2- c]-1,3,2-oxazaphospholidin}-2-yl 2,-deoxyribonucleoside (Sc- 2) (Agrawal strategy). The azolium triflates allowed the stereoselective formation of an internucleotide phosphorothioate bond via the above-described condensation using a stereochemically pure phosphoramidite, followed by sulfurization using bis[3-triethoxysilylpropyl]tetrasulfide. The highest diastereoexcess values of the products in the synthesis of dideoxyribonucleoside phosphorothioates using a suitable azolium triflate such as benzimidazolium triflate, N -methylbenzimidazolium triflate or N -phenylimidazolium triflate were 90,96,% in solution phase or 80,88,% in solid phase; these values were higher than those obtained in the synthesis using 1H -tetrazole as a promoter for the condensation of a nucleoside phosphoramidite and a nucleoside. This paper also describes that studies on the absolute configurations of stereogenic phosphorus atoms in the phosphoramidites Rc- 1 and Sc- 2 by meansof two different existing methods, i.,e., the Beaucage method, gave contrary conclusions, and thus the configurations should be determined by an absolutely reliable method, such as X-ray analysis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) [source]


    Stereoselective Synthesis of C- and N-Ketosides by Lewis Acid-Catalyzed C- and N-Glycosidation of Alkynyl, Phenyl, and Methyl Ketoses

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 24 2003
    Ana M. Gómez
    Abstract C-Ketosides can be prepared conveniently, in a stereoselective manner, from alkynyl, phenyl and methyl glucopyranose hemiketals by reaction with carbon nucleophiles in the presence of Lewis acids. The reaction of the hemiketals with trimethylsilyl azide provides an efficient route to the corresponding N-ketopyranosides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]


    Stereoselective Synthesis of myo -, neo -, L - chiro, D - chiro, allo -, scyllo -, and epi -Inositol Systems via Conduritols Prepared from p -Benzoquinone

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 10 2003
    Michael Podeschwa
    Abstract A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo -, L - chiro -, D - chiro -, epi -, scyllo -, allo -, and neo -inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p -benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]


    A Rapid and Efficient Stereoselective Synthesis of (Z)- and (E)-Allyl Bromides from Baylis,Hillman Adducts Using Bromo(dimethyl)sulfonium Bromide,

    HELVETICA CHIMICA ACTA, Issue 7 2006
    Biswanath Das
    Abstract Treatment of Baylis,Hillman adducts 1 with bromo(dimethyl)sulfonium bromide, Br(Me2)S+Br,, in MeCN was found to stereoselectively afford (Z)- and (E)-allyl bromides 2. The reaction is rapid at room temperature, high-yielding, and highly stereoselective. [source]


    Stereoselective Synthesis of Tetrahydrofuran Spiro- , -Lactams by Ru-Catalyzed Metathesis of 7-Oxabicyclo[2.2.1]heptenes

    HELVETICA CHIMICA ACTA, Issue 6 2005
    Aurelio
    A new method for the synthesis of spiro- , -lactams tethered to tetrahydrofuran rings is described. The procedure is based on Ru-catalyzed metathesis sequences with oxanorbornene precursors easily obtained by the Staudinger [2+2] cycloaddition of related imines. [source]


    Stereoselective Synthesis of ,-Proline Derivatives from Allylamines via Domino Hydroformylation/Wittig Olefination and Aza-Michael Addition

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 6 2010
    Andreas Farwick
    Abstract Under appropriate reaction conditions, a domino hydroformylation/Wittig olefination can be accomplished with derivatives of allylamines and stabilized Wittig ylides. A further highly diastereoselective aza-Michael reaction yields ,-proline derivatives. These are, for example, useful as building blocks for alkaloid syntheses. [source]


    A New Stereoselective Synthesis of Cyclopropanes Containing Quaternary Stereocentres via Organocatalytic Michael Addition to Vinyl Selenones

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 11-12 2009
    Francesca Marini
    Abstract A novel organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of ,-substituted cyanoacetates to easily accessible vinyl selenones catalyzed by a bifunctional ureidic catalyst, smoothly cyclize by intramolecular alkylation induced by a de-ethoxycarbonylation process. The one-pot sequence generates cyclopropanes bearing adjacent tertiary and quaternary stereocentres as single Z -isomers in moderate to high yields and good enantiomeric excesses. [source]


    Stereoselective Synthesis of Metalated Cyclobutyl Derivatives

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 7-8 2009
    Einav Tsoglin
    Abstract Treatment of Z -vinyl carbamates with dicyclopentadienyl(diethyl)zirconium [Et2ZrCp2] leads to cyclobutyl-zirconocene derivatives in good yields and as a unique diastereoisomer. The reaction proceeds through a carbometalative ring-expansion followed by an intramolecular migratory insertion. [source]


    Stereoselective Synthesis of Conjugated Bisallenols as Precursors of Novel Bis(2,5-dihydrofuran) Derivatives

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 1-2 2009
    Manojkumar Poonoth
    Abstract A stereoselective synthesis of conjugated bis(,-hydroxyallenes) by copper-mediated SN2,-substitution is described. Their silver- or gold-catalyzed cycloisomerization affords highly functionalized 2-allenyl-substituted 2,5-dihydrofurans and bis(2,5-dihydrofurans) under axis-to-center chirality transfer. [source]


    Stereoselective Synthesis of Three Isomers of tert -Butyl 5-Hydroxy-4-methyl-3-oxohexanoate through Alcohol Dehydrogenase-Catalyzed Dynamic Kinetic Resolution

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 1-2 2009
    Steffen Lüdeke
    Abstract Regioselective reduction of the 5-keto group of tert -butyl 4-methyl-3,5-dioxohexanoate (1) leads to a stereodiad of tert -butyl 5-hydroxy-4-methyl-3-oxohexanoate (2). Alcohol dehydrogenases from Lactobacillus brevis (LBADH), Rhodococcus sp. (RS 1-ADH) and Saccharomyces cerevisiae (YGL157w) reduce 1 under dynamic kinetic resolution conditions, thereby establishing two chiral carbons with a single reduction step. While it had been shown previously that LBADH reduction of 1 stereoselectively leads to syn -(4S,5R)- 2, alcohol dehydrogenase-mediated dynamic kinetic resolution now allows easy access to syn -(4R,5S)- 2 (RS 1-ADH; 97.6% ee, syn:anti=92:8, 66% conversion, 37% isolated yield) and anti -(4S,5S)- 2 (YGL157w; 90% ee, anti:syn=93:7, 64% conversion, 42% isolated yield), as well. Thus three out of four possible stereoisomers were formed selectively upon reduction of 1. [source]


    Efficient Stereoselective Synthesis of Nitrocyclopropanes by the Oxidative Cyclization of Michael Adducts of Nitroolefins with Activated Methylene Compounds

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 16 2008
    Renhua Fan
    Abstract An efficient oxidative cyclopropanation of the Michael adducts of nitroolefins with activated methylene compounds by the combination of iodobenzene diacetate and tetrabutylammonium iodide is reported. Highly functionalized nitrocyclopropanes are synthesized in moderate to good yields via the Michael addition and cyclopropanation with high diastereoselectivity and enantioselectivity under mild conditions. [source]


    Stereoselective Synthesis of Multifunctionalized 1,2,4-Triazolidines by a Ruthenium Porphyrin-Catalyzed Three-Component Coupling Reaction

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 16-17 2006
    Ming-Zhong Wang
    Abstract Multifunctionalized 1,2,4-triazolidines have been synthesized by a ruthenium porphyrin-catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed the in situ generation of azomethine ylides from ,-diazo esters and imines. Stereoselective 1,3-dipolar cycloaddition reactions of the azomethine ylides with dialkyl azodicarboxylates gave the corresponding 1,2,4-triazolidines in good yields (up to 85,%). Using chiral 8-phenylmenthanol ,-diazo ester as the carbenoid source, chiral 1,2,4-triazolidines have been obtained with good diastereoselectivity (up to 84,% de). Some of the 1,2,4-triazolidines exhibited good cytotoxicity against human nasopharyngeal carcinoma (SUNE1) (IC50=10.4,,M) and human cervical carcinoma (Hela) (IC50=10.7,,M) cell lines. [source]


    Highly Stereoselective Synthesis of Arylene-Silylene-Vinylene Polymers

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 9 2005
    Mariusz Majchrzak
    Abstract Stereoregular trans -arylene-silylene-vinylene polymers of Mw=13100,34800 and PDI=1.6,2.9 of the general formulas CH2CH[SiMe2C6H4 -SiMe2CHCH](16, 17, 18) and CH2CH[(R)CHCHC6H4CHCH](where R=Me2Si- pC6H4 - SiMe2, Me2Si- mC6H4SiMe2 and Me2SiC6H4C6H4SiMe2) (19, 20, 21) have been effectively synthesized via silylative coupling (SC) homopolycondensation of bis(vinyldimethylsilyl)arenes (10, 12, 14) and cross-polycondensation of 4-(vinyldimethylsilyl)styrene (11) as well as cross-copolycondensation of bis(vinyldimethylsilyl)arenes (10, 12 and 14) with 1,4-divinylbenzene (9) catalyzed by [RuH(Cl)(CO)(PCy3)2] (7). Such highly stereoregular products cannot be synthesized via ADMET polycondensation or ring opening metathesis ROM or polyaddition of hydridosilanes to acetylenes. [source]


    Highly Stereoselective Synthesis of Novel Multistereogenic Bis - Bifunctional Ligands Based on [2.2]Paracyclophane- 4,7-quinone, their Structure Elucidation and Application in Asymmetric Catalysis

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 1 2005
    Natalia Vorontsova
    Abstract Bis - bifunctional cis -4,7-diarylsubstituted-4,7-dihydroxy-4,7-dihydro[2.2]paracyclophanes 3,6 were synthesized by a highly diastereoselective reaction of ortho -substituted aryllithium reagents with [2.2]paracyclophane-4,7-quinone (1). Enantiomerically pure diols 3,5 were tested as chiral inductors in the enantioselective addition of diethylzinc to benzaldehyde (up to 93.5% ee). Acid dehydration of cis -4,7-di(2-methoxyphenyl)-4,7-dihydroxy-4,7-dihydro[2.2]paracyclophane (3) results in 4,7-dihydro-7,8-di(2-methoxyphenyl)[2.2]paracyclophane-4-one (8) , a planar chiral cyclohexadienone of the [2.2]paracyclophane series with a para -semiquinoid substructure. X-Ray investigations of compounds 3, 4 and 8 were performed. [source]


    Stereoselective Synthesis of Tertiary Ethers through Geometric Control of Highly Substituted Oxocarbenium Ions,

    ANGEWANDTE CHEMIE, Issue 34 2010
    Lei Liu
    Vollständig substituiert heißt vollständig kontrolliert: Die Geometrie in 1,1-disubstituierten Oxocarbeniumionen und die Konformation von Oxocarbeniumionen, die ein tertiäres Stereozentrum enthalten, lassen sich mithilfe einfacher Modelle vorhersagen. Auf diesen Modellen beruhen hoch stereoselektive Synthesen von Tetrahydropyran-Derivaten mit tertiären Ethergruppen (siehe Schema; RL, RS und RN sind große, kleine bzw. nucleophile Gruppen). [source]


    Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions,

    ANGEWANDTE CHEMIE, Issue 31 2010
    Anass Znabet
    Ideal kombiniert: Optisch reine 3,4-disubstituierte 1-Pyrroline, die aus entsprechenden meso -Pyrrolidinen durch biokatalytische Desymmetrisierung mit Monoaminoxidase,N (MAO-N) erhalten wurden, reagieren mit Carbonsäuren und Isocyaniden in einer Ugi-Mehrkomponentenreaktion hoch diastereoselektiv zu substituierten Prolylpeptiden mit großer Bedeutung in der Pharmazie. [source]