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  • Title: Highly enantioselective and regioselective carbonyl reduction of cyclic alpha,beta-unsaturated ketones using TarB-NO2 and sodium borohydride.
    Author: Kim J, Bruning J, Park KE, Lee DJ, Singaram B.
    Journal: Org Lett; 2009 Oct 01; 11(19):4358-61. PubMed ID: 19711968.
    Abstract:
    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.
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