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.
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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β-Amino Alcohols, Esters, Oxygen, Organocatalysis