Enantio- and Diastereoselective, Stereospecific Mannich-Type Reactions in Water

Tomoaki Hamada, Kei Manabe, and Shū Kobayashi*
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
J. Am. Chem. Soc., 2004, 126 (25), pp 7768–7769
DOI: 10.1021/ja048607t
Publication Date (Web): June 4, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, skobayas@mol.f.u-tokyo.ac.jp

Abstract

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Catalytic asymmetric Mannich-type reactions in water proceeded in high yields and selectivities using a combination of ZnF2 and a chiral diamine that has the methoxy groups on the aromatic rings. In these reactions, either syn- or anti-Mannich adducts were stereospecifically obtained from (E)- or (Z)-silicon enolate, in contrast with most asymmetric Mannich-type reactions.

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History

  • Published In Issue June 30, 2004
  • Received March 10, 2004

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