l-Piperazine-2-carboxylic Acid Derived N-Formamide as a Highly Enantioselective Lewis Basic Catalyst for Hydrosilylation of N-Aryl Imines with an Unprecedented Substrate Profile

Zhouyu Wang,†§ Mounuo Cheng,† Pengcheng Wu,†‡ Siyu Wei,† and Jian Sun*†
Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China, and Department of Chemistry, Xihua University, Chengdu 610039, China
Org. Lett., 2006, 8 (14), pp 3045–3048
DOI: 10.1021/ol060984i
Publication Date (Web): June 6, 2006
Copyright © 2006 American Chemical Society
†

 Chengdu Institute of Biology.

,
§

 Xihua University.

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‡

 Chengdu 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.

, sunjian@cib.ac.cn

Abstract

Abstract Image

l-Piperazine-2-carboxylic acid derived N-formamides have been developed as highly enantioselective Lewis basic catalysts for the hydrosilylation of N-aryl imines with trichlorosilane. The arene sulfonyl group on N4 was found to be critical for the high enantioselectivity of the catalyst. High isolated yields (up to 99%) and enantioselectivities (up to 97%) were obtained for a broad range of substrates, including aromatic and aliphatic ketimines, particularly those with R2 as relatively bulky alkyl groups.

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History

  • Published In Issue July 06, 2006
  • Received April 25, 2006

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