Unexpected Ring-Opening Reactions of Aziridines with Aldehydes Catalyzed by Nucleophilic Carbenes under Aerobic Conditions

Yan-Kai Liu,† Rui Li,‡ Lei Yue,† Bang-Jing Li,‡ Ying-Chun Chen,*† Yong Wu,† and Li-Sheng Ding‡
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China, and Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China
Org. Lett., 2006, 8 (8), pp 1521–1524
DOI: 10.1021/ol0529905
Publication Date (Web): March 23, 2006
Copyright © 2006 American Chemical Society
†

 Sichuan University.

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‡

 Chengdu Institute of Biology.

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*

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

, ycchenhuaxi@yahoo.com.cn

Abstract

Abstract Image

The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened β-amino ketones, were exclusively obtained. A plausible mechanism for this unprecedented carbene-mediated reaction was also proposed.

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History

  • Published In Issue April 13, 2006
  • Received December 10, 2005

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