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Chiral N-Heterocyclic Carbene Catalyzed Staudinger Reaction of Ketenes with Imines: Highly Enantioselective Synthesis of N-Boc β-Lactams

Yan-Rong Zhang, Lin He, Xu Wu, Pan-Lin Shao and Song Ye*

*Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China, Email: songyeiccas.ac.cn

Y.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye, Org. Lett., 2008, 10, 277-280.

DOI: 10.1021/ol702759b (free Supporting Information)


Abstract

A chiral N-heterocyclic carbene catalyzed the Staudinger reaction of arylalkylketenes with a variety of N-tert-butoxycarbonyl arylimines to give the corresponding cis-β-lactams in good yields with good diastereoselectivities and excellent enantioselectivities.


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Formal Cycloaddition of Disubstituted Ketenes with 2-Oxoaldehydes Catalyzed by Chiral N-Heterocyclic Carbenes

L. He, H. Lv, Y.-R. Zhang, S. Ye, J. Org. Chem., 2008, 73, 8101-8103.


Key Words

Staudinger Synthesis, β-Lactams, Organocatalysis


ID: J54-Y2008-0150