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Highly enantioselective and regioselective carbonyl reduction of cyclic alpha,beta-unsaturated ketones using TarB-NO2 and sodium borohydride. 2009

Jinsoo Kim, and John Bruning, and Kevin E Park, and David J Lee, and Bakthan Singaram
Department of Chemistry and Biochemistry, University of California Santa Cruz, 1156 High Street, Santa Cruz, California 95064, USA.

Asymmetric 1,2-reduction of alpha,beta-unsaturated ketones using TarB-NO(2) and NaBH(4) is reported. Simple cycloalkenones give products in low enantiomeric excess. However, cycloalkenones with alpha-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols in enantiomeric excess up to 99%. The starting materials for TarB-NO(2) are inexpensive, and the boronic acid can be easily recovered in high yield by a simple acid extraction.

UI MeSH Term Description Entries
D007659 Ketones Organic compounds containing a carbonyl group Ketone
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D001894 Borohydrides A class of inorganic or organic compounds that contain the borohydride (BH4-) anion. Borohydride
D001897 Boronic Acids Inorganic or organic compounds that contain the basic structure RB(OH)2. Boronic Acid,Acid, Boronic,Acids, Boronic
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D020005 Propanols Isomeric forms and derivatives of PROPANOL (C3H7OH). Alcohols, Propyl,Propyl Alcohols

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