Synthesis 2008(8): 1319-1322  
DOI: 10.1055/s-2008-1032017
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of β-Amino Esters by a Chiral Brønsted Acid Catalyzed Mannich-Type Reaction

Junji Itoh, Kohei Fuchibe, Takahiko Akiyama*
Department of Chemistry, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
Fax: +81(3)59921029; e-Mail: takahiko.akiyama@gakushuin.ac.jp;
Further Information

Publication History

Received 5 September 2007
Publication Date:
10 January 2008 (online)

Abstract

Mannich-type reactions of ketene silyl acetals with aldimines proceeded smoothly under the influence of 10 mol% of a cyclic chiral phosphate derivative derived from (R)-BINOL as a chiral Brønsted acid catalyst to furnish β-amino esters with excellent enantio­selectivities.

8

For a review, see: Ting, A.; Schaus, S. E. Eur. J. Org. Chem., in press.

14

For the preparation of 3c, see ref. 9b.