Lithiation-induced migrations from nitrogen to carbon in terminal aziridines

被引:44
作者
Hodgson, David M.
Humphreys, Philip G.
Xu, Zhaoqing
Ward, John G.
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] GlaxoSmithKline, Neurol & CI Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England
关键词
amino acids; aziridines; lithiation; rearrangement; synthetic methods;
D O I
10.1002/anie.200604920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valuable trans-aziridinylesters and trans- aziridinylphosphonates. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2245 / 2248
页数:4
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