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Homoallylic Alcohols (homoallylic + alcohol)

Distribution by Scientific Domains
Chemistry100%
Distribution within Chemistry
Organic Chemistry75%
General & Introductory Chemistry24%

Kinds of Homoallylic Alcohols

  • tertiary homoallylic alcohol
    		•

    Selected Abstracts

    ChemInform Abstract: From Allylic Alcohols to Chiral Tertiary Homoallylic Alcohol: Palladium-Catalyzed Asymmetric Allylation of Isatins.

    CHEMINFORM, Issue 46 2009
    Xiang-Chen Qiao
    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]

    The First Example of Enantioselective Allyl Transfer from a Linear Homoallylic Alcohol to an Aldehyde.

    CHEMINFORM, Issue 51 2002
    Teck-Peng Loh
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    ChemInform Abstract: Formation of Tetrahydrofuran from Homoallylic Alcohol via a Tandem Sequence: 2-Oxonia [3,3]-Sigmatropic Rearrangement/Cyclization Catalyzed by In(OTf)3.

    CHEMINFORM, Issue 26 2001
    Teck-Peng Loh
    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: Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes Leading to Secondary Homoallylic Alcohols.

    CHEMINFORM, Issue 49 2009
    Yasushi Obora
    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]

    MgI2 Etherate-Promoted Allylation of Aldehydes: Simple and Efficient Synthesis of Homoallylic Alcohols.

    CHEMINFORM, Issue 52 2007
    Xingxian Zhang
    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]

    Simple, One-Pot Procedure for the Generation of Homoallylic Alcohols from Barbier-Type Allylation of Gem-Diacetates in the Presence of ,-Cyclodextrin in Water.

    CHEMINFORM, Issue 45 2007
    M. Somi Reddy
    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]

    Dibutyltin Oxide Catalyzed Allyl-Transfer Reaction from Tertiary Homoallylic Alcohols to Aldehydes.

    CHEMINFORM, Issue 50 2006
    Akira Yanagisawa
    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]

    Synthesis of Homoallylic Alcohols from Ketones in Water.

    CHEMINFORM, Issue 23 2006
    Jun Wang
    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]

    Copper-Catalyzed Highly Enantioselective Synthesis of Cyclic Allylic and Homoallylic Alcohols with Dialkylzinc Reagents.

    CHEMINFORM, Issue 28 2005
    Mauro Pineschi
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    Chemoselective Allylation of Aldehydes Using Cerium(III) Chloride: Simple Synthesis of Homoallylic Alcohols.

    CHEMINFORM, Issue 23 2005
    J. S. Yadav
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    A Convenient Synthesis of Substituted 3-Bromotetrahydrofurans from Homoallylic Alcohols.

    CHEMINFORM, Issue 10 2005
    Marina V. Chirskaya
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    A Rapid and Convenient Synthesis of Homoallylic Alcohols by the Barbier,Grignard Reaction.

    CHEMINFORM, Issue 7 2005
    Grant J. Sormunen
    No abstract is available for this article. [source]

    Titanium-Mediated [2 + 2 + 2] Coupling of Diynes with Homoallylic Alcohols.

    CHEMINFORM, Issue 40 2003
    Moo Je Sung
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    Addition of Water to Arylidenecyclopropanes: A Highly Efficient Method for the Preparation of gem-Aryl Disubstituted Homoallylic Alcohols.

    CHEMINFORM, Issue 37 2003
    Amal I. Siriwardana
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    Asymmetric Epoxidation of Homoallylic Alcohols and Application in a Concise Total Synthesis of (-)-,-Bisabolol and (-)-8-epi-,-Bisabolol.

    CHEMINFORM, Issue 25 2003
    Naoya Makita
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    PCC-Mediated Novel Oxidation Reactions of Homobenzylic and Homoallylic Alcohols.

    CHEMINFORM, Issue 17 2003
    Rodney A. Fernandes
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    Preparation of Homoallylic Alcohols by Nickel-Catalyzed Cyclizations of Allenyl Aldehydes.

    CHEMINFORM, Issue 13 2003
    John Montgomery
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    Synthesis of Diastereomerically Enriched Cyclic Homoallylic Alcohols Using Molybdenum ,-Allyl Complexes.

    CHEMINFORM, Issue 51 2002
    Marie E. Krafft
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]

    ChemInform Abstract: Intramolecular Hydrosilylation and Silicon-Assisted Cross-Coupling: An Efficient Route to Trisubstituted Homoallylic Alcohols.

    CHEMINFORM, Issue 18 2001
    Scott E. Denmark
    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: Reaction of Homoallylic Alcohols with NaIO4/NaHSO3 Reagent,Synthesis of Alkyl-Substituted Tetrahydrofuran Derivatives.

    CHEMINFORM, Issue 15 2001
    Yoshio Okimoto
    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]

    Rhodium-Catalyzed Allylation of Aldehydes with Homoallylic Alcohols by Retroallylation and Isomerization to Saturated Ketones with Conventional or Microwave Heating

    CHEMISTRY - AN ASIAN JOURNAL, Issue 1 2008
    Yuto Sumida
    Abstract The treatment of an aldehyde with a tertiary homoallylic alcohol at 100,250,°C in the presence of cesium carbonate and a rhodium catalyst leads to allyl transfer from the homoallylic alcohol to the aldehyde. The process includes Rh-mediated retroallylation to form an allyl rhodium species as the key intermediate. The homoallylic alcohol formed initially through allyl transfer is converted under the reaction conditions into the corresponding saturated ketone when bulky ligands are used. Microwave heating at 250,°C accelerates the reaction significantly. [source]

    Bismuth Triflate Catalyzed Allylation of Aldehydes with Allylstannane under Microwave Assistance,

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 34 2007
    Thierry Ollevier
    Abstract In the presence of a catalytic amount of bismuth triflate and under microwave irradiation, mixtures of aldehyde and allylstannane afforded smoothly the corresponding homoallylic alcohol. A wide variety of aldehydes were treated under these conditions. The reactions proceeded rapidly and afforded smoothly the corresponding homoallylic alcohol in good to very good yields using catalytic amounts of Bi(OTf)3·4H2O (0.5 mol-%) and under microwave irradiation for a short time.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source]

    On the Scope of a Prins -Type Cyclization of Oxonium Ions

    HELVETICA CHIMICA ACTA, Issue 11 2004
    Georg Fráter
    The Prins cyclization of an aldehyde 1 with a homoallylic alcohol 2, affording tetrahydro-2H -pyrans 4via the oxonium ion 3 as central intermediate, was conceptually transferred to (alk-3-enyloxy)acrylates 6, which form a related oxonium ion 7 upon treatment with acids (Scheme,1). The scope and utility of this modification of the Prins -type cyclization of oxonium ions is discussed exemplarily by means of the syntheses of ten tetrahydro-2H -pyran and tetrahydrofuran derivatives, featuring diverse substitution patterns as well as different degrees of molecular complexity. These target structures include (±)-ethyl (2RS)-2-[(2RS,4SR,6RS)- and (2SR,4RS,6SR)-2-tetahydro-4-hydroxy-6-methylpyran-2-yl]propanoate (23), (±)-ethyl [(2RS, 3RS)-tetrahydro-3-isopropenylfuran-2-yl]acetate (32), (±)-ethyl (2Z)-3-(tetrahydro-2,2-dimethylfuran-3-yl)acrylate (37), (±)-(3aRS,6RS, 7aRS)-octahydro-7a-methylbenzofuran-6-yl formate (42), (±)-ethyl (2RS,3RS,4aRS,8SR,8aRS)-hexahydro-2,5,5,8-tetramethyl-7-oxo-2H,5H -pyrano[4,3- b]pyran-3-carboxylate (48), and (±)-ethyl (2RS,3RS,6SR)-tetrahydro-6-(2-methoxy-2-oxoethyl)-3-methyl-2H -pyran-2-carboxylate (53) (see Schemes,3 and 5,8). Besides the stereochemistry and mechanistic details of this versatile oxonium-ion cyclization, the synthesis of suitable starting materials is also described. [source]

    Asymmetric Allylation of Methyl Ketones by Using Chiral Phenyl Carbinols

    CHEMISTRY - A EUROPEAN JOURNAL, Issue 25 2009

    Abstract To methyl or to alkyl? High induced facial selectivities and excellent yields are obtained in the allylation of aliphatic methyl ketones by using a structurally simple phenylbenzyl auxiliary to give the corresponding homoallylic ethers (see scheme). The transferred auxiliary has a very good protecting quality and can easily be removed. Novel chiral auxiliaries for the stereoselective allylation of aliphatic methyl ketones with allyltrimethylsilane and their use in the synthesis of homoallylic ethers are described. In a multicomponent domino process catalyzed by trifluoromethanesulfonic acid, the allyl moiety and the auxiliary are transferred onto the substrate to yield tertiary homoallylic ethers. The most useful auxiliary for a general application turned out to be the trimethylsilyl ether of phenyl benzyl carbinol with an induced diastereoselectivity of 90:10 using ethyl methyl ketone and 94:6 using isopropyl methyl ketone as substrates. The transferred substituted benzyl moiety has good protecting properties in subsequent transformations and can easily be removed under reductive conditions to provide the corresponding homoallylic alcohol. The origin of the high selectivity could be elucidated by identifying the relevant transition states using quantum-chemical calculations. An excellent agreement between calculated and experimentally observed selectivities was obtained assuming an oxocarbenium ion as intermediate. [source]

    From Solution-Phase to Solid-Phase Enyne Metathesis: Crossover in the Relative Performance of Two Commonly Used Ruthenium Pre-Catalysts

    CHEMISTRY - A EUROPEAN JOURNAL, Issue 17 2005
    Dominic E. A. Brittain Dr.
    Abstract A crossover in the ability of two distinct ruthenium-based metathesis pre-catalysts to effect the synthesis of dialkenylboronic esters in solution and on the solid-phase was observed. Specifically, while the Grubbs 2nd generation pre-catalyst 3 affords a greater degree of conversion to product than the Hoveyda,Grubbs pre-catalyst 2 in a solution-phase enyne-metathesis reaction, this trend is reversed in the solid-phase variant. Systematic investigation showed this trend to be general, regardless of variations in the homoallylic alcohol and alkynylboronic ester components of the reaction, as well as in the type of solid support employed. Experiments to determine a mechanistic hypothesis for this trend highlighted the significance of the ruthenium remaining bound to the substrate after metathetic rearrangement and found the presence of phosphine ligand to be detrimental to the success of the solid-phase reaction. Therefore, these results suggest an expanded role for phosphine-free pre-catalysts, such as 2, in challenging solid-phase metathesis reactions. [source]

    Rhodium-Catalyzed Allylation of Aldehydes with Homoallylic Alcohols by Retroallylation and Isomerization to Saturated Ketones with Conventional or Microwave Heating

    CHEMISTRY - AN ASIAN JOURNAL, Issue 1 2008
    Yuto Sumida
    Abstract The treatment of an aldehyde with a tertiary homoallylic alcohol at 100,250,°C in the presence of cesium carbonate and a rhodium catalyst leads to allyl transfer from the homoallylic alcohol to the aldehyde. The process includes Rh-mediated retroallylation to form an allyl rhodium species as the key intermediate. The homoallylic alcohol formed initially through allyl transfer is converted under the reaction conditions into the corresponding saturated ketone when bulky ligands are used. Microwave heating at 250,°C accelerates the reaction significantly. [source]

    Indium Triiodide Catalyzed Direct Hydroallylation of Esters

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 18 2010
    Yoshihiro Nishimoto
    Abstract The InI3 -catalyzed hydroallylation of esters by using hydro- and allysilanes under mild conditions has been accomplished. Many significant groups such as alkenyl, alkynyl, cyano, and nitro ones survive under these conditions. This reaction system provided routes to both homoallylic alcohols and ethers, in which either elimination of the alkoxy moiety or of the carbonyl oxygen atom could be freely selected by changing the substituents on the alkoxy moiety and on the hydrosilane. In addition, the hydroallylation of lactones took place without ring cleavage to produce the desired cyclic ethers in high yields. [source]

    Diastereoselective Zinc-Mediated Barbier-Type Allylation and Propargylation of 3-Formylcephalosporins

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 9 2003
    Rolf Keltjens
    Abstract We describe the allylation and propargylation of 3-formylcephalosporins under zinc-mediated, aqueous Barbier conditions, from which the corresponding homoallylic alcohols are produced in good yields and with good-to-excellent diastereoselectivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]

    Internal Nucleophilic Termination in Acid-Mediated Polyene Cyclizations Part 4,

    HELVETICA CHIMICA ACTA, Issue 12 2005
    Synthetic Access to Tetracyclic Didehydro, Tetradehydro Analogues of (±)- Ambrox®
    Treatment of the unsaturated bicyclic homoallylic alcohols (E)- and (Z)- 5 and (Z)- and (E)- 10 and allenic alcohol 16 with an excess of ClSO3H in 2-nitropropane or CH2Cl2 at ,,80° afforded, in moderate yields (ca. 30,70%), diastereoisomer mixtures of racemic tetracyclic ethers 12a,c (Table,1) and 17a,b (Table,2), respectively. These kinetically controlled stereospecific transformations are believed to proceed via concerted or nonconcerted pathways (see Schemes,4 and 6) and the results are fully consistent with our earlier work. Representing novel didehydro bridged analogues of known, olfactively active labdane tricyclic ethers, the organoleptic properties of 12a,c and 17a,b are briefly described, especially those of 12c which, in the context of structure,activity studies, is a racemic didehydro analogue of the known ambergris odorant Ambrox®. [source]

    Iron(III) Chloride-Catalyzed Direct Sulfonylation of Alcohols with Sodium Arenesulfinates

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 11-12 2010
    M. Amarnath Reddy
    Abstract A new protocol for the direct sulfonylation of benzylic, allylic and homoallylic alcohols with sodium arenesulfinates is described by using iron(III) chloride as a catalyst and chlorotrimethylsilane as an additive. This method requires no preactivation of alcohols. Surprisingly in the reaction with homoallyl alcohols nucleophilic addition of sulfinate anion, occurs at the terminal double bond instead of nucleophic substitution at the alcohol. [source]