A Highly Efficient and Direct Approach for Synthesis of Enantiopure β-Amino Alcohols by Reductive Cross-Coupling of Chiral N-tert-Butanesulfinyl Imines with Aldehydes

Yu-Wu Zhong,† Yi-Zhou Dong,† Kai Fang,† Kenji Izumi,† Ming-Hua Xu,*†‡ and Guo-Qiang Lin*†
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, and Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China
J. Am. Chem. Soc., 2005, 127 (34), pp 11956–11957
DOI: 10.1021/ja054401w
Publication Date (Web): August 6, 2005
Copyright © 2005 American Chemical Society
†

 Shanghai Institute of Organic Chemistry.

,
*

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

,
‡

 Shanghai Institute of Materia Medica.

, xumh@mail.sioc.ac.cn

Abstract

Abstract Image

A highly efficient and practical approach for the synthesis of optically pure β-amino alcohols by the SmI2-induced reductive cross-coupling of chiral N-tert-butanesulfinyl imines with aldehydes was developed. This method allows the preparation of a broad range of chiral β-amino alcohols, including functionalized ones under mild conditions. It provides a straightforward access to enantiopure β-amino alcohols that are widely applicable in asymmetric synthesis.

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History

  • Published In Issue August 31, 2005
  • Received July 4, 2005

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