Asymmetric Reduction of Ketones Under Mild Conditions Using NaBH 4  and TarB‐NO 2 : An Efficient and Unusual Chiral Acyloxyborohydride Reducing System | Zendy

Cordes David B. | Zendy; Nguyen Thao M. | Zendy; Kwong Tracey J. | Zendy; Suri Jeff T. | Zendy; Luibrand Richard T. | Zendy; Singaram Bakthan | Zendy

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Asymmetric Reduction of Ketones Under Mild Conditions Using NaBH 4 and TarB‐NO 2 : An Efficient and Unusual Chiral Acyloxyborohydride Reducing System

Author(s) -

Cordes David B.,

Nguyen Thao M.,

Kwong Tracey J.,

Suri Jeff T.,

Luibrand Richard T.,

Singaram Bakthan

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500397

Subject(s) - chemistry , reagent , bifunctional , tartaric acid , enantiomer , reducing agent , lewis acids and bases , combinatorial chemistry , organic chemistry , ketone , enantioselective synthesis , catalysis , citric acid

High enantioselectivities are obtained for the reduction of a series of ketones using the inexpensive and mild reducing agent NaBH 4 with TarB‐NO 2 ( 1 ). This easily prepared tartaric acid‐based reagent combines a Lewis acid with carboxylic acids in a single bifunctional reagent. When combined with NaBH 4 , the resulting chiral acyloxyborohydride mediates the reduction of aromatic ketones to provide the product alcohols in enantiomeric excesses of 93–98 %. Several aliphatic ketones were also reduced with moderate to excellent enantioselectivity. A unique mechanism is provided with supporting calculations for the proposed active species and transition state. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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