Download PDF
Synlett 1997; 1997(2): 217-218
DOI: 10.1055/s-1997-725
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Hydroxypinanone as Chiral Auxiliary in Michael Additions: an Inversion of Diastereoselectivity at Low Concentration of Enolate, a Substrate-Directed Approach

Arlette Solladié-Cavallo* , Jean-Luc Koessler, Thomas Isarno, Didier Roche, Rindra Andriamiadanarivo
  • *Laboratoire de Stéréochimie Organométallique associé au CNRS, ECPM/ULP, 1 rue Blaise Pascal, 67008-Strasbourg, France, Internet ascava@chimie.u.strasbg.fr
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Inversion of diastereoselectivity (from 90-98% S to 90-95% R) was observed for Michael additions as a function of the starting chiral enolate concentration. It is also shown that catalytic amount of a phosphazene base (t-Oct-P2) allowed rapid reaction (1h), total conversion and high (90%) R-diastereoselectivity.

diastereoselectivity - hydroxypinanone - phosphazene bases - substrate-directed approach - Michael additions