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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, Email: ycchenhuaxiyahoo.com.cn

Y.-K. Liu, R. Li, L. Yue, B.-J. Li, Y.-C. Chen, Y. Wu, L.-S. Ding, Org. Lett., 2006, 8, 1521-1524.

DOI: 10.1021/ol0529905 (free Supporting Information)


Abstract

The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene gave carboxylates of 1,2-amino alcohols. A plausible mechanism for this reaction is discussed.

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Key Words

β-Amino Alcohols, Esters, Oxygen, Organocatalysis


ID: J54-Y2006-960