Synthesis 2008(23): 3874-3876  
DOI: 10.1055/s-0028-1083605
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Mild and Practical Reductions of Prochiral Ketones to Chiral Alcohols Using the Chiral Boronic Ester TarB-H

Scott Eagon, Jinsoo Kim, Bakthan Singaram*
Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, CA 95064, USA
Fax: +1(831)4592935; e-Mail: [email protected];
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Publikationsverlauf

Received 29 July 2008
Publikationsdatum:
06. November 2008 (online)

Abstract

Chiral alcohols are prepared under mild conditions in high enantiomeric excesses using the tartaric acid derived chiral boronic ester TarB-H. The phenylboronic acid was quantitatively recovered and recycled using a simple extraction with sodium hydroxide and diethyl ether. Aromatic and aliphatic secondary alcohols were prepared in up to 99% ee.

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Phenylboronic acid costs approximately $430/mol and 3-nitrophenylboronic acid $1600/mol.