Synlett 2002(1): 0026-0028
DOI: 10.1055/s-2002-19336
LETTER
© Georg Thieme Verlag Stuttgart · New York

Proline-Catalyzed Enantioselective Michael Additions of Ketones to Nitrostyrene

Dieter Enders*, Atsushi Seki
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: Enders@RWTH-Aachen.de;
Further Information

Publication History

Received 24 September 2001
Publication Date:
01 February 2007 (online)

Abstract

Proline-catalyzed Michael additions of ketones to nitrostyrene were examined to obtain optically active γ-nitro ketones. The catalytic asymmetric 1,4-additions afforded the desired γ-nitro ketones in medium to excellent yields and up to 97% de of the syn-diastereomers and 76% ee.

1

On leave from the Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan.

11

The reaction using (S)-proline in DMSO resulted in an enantiomeric excess of 7% ee and a yield of 97%. [7a]

12

The reaction in DMSO gave (S,R)-3f in high yield but low enantioselectivity by employing 15 mol% of (S)-proline. [7a]