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Synlett 1997; 1997(2): 217-218
DOI: 10.1055/s-1997-725
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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
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Publikationsdatum:
31. Dezember 2000 (online)

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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