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: songye
iccas.ac.cn
Y.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye, Org. Lett., 2008, 10, 277-280.
DOI: 10.1021/ol702759b
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.
see article for more examples
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
