α,β-氮丙啶膦酸酯通过氮到碳的磷酰基迁移由氨基锂诱导生成在末端氮丙啶中。
α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines.
机构信息
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
出版信息
Beilstein J Org Chem. 2010 Oct 13;6:978-83. doi: 10.3762/bjoc.6.110.
Abstract
N-Phosphonate terminal aziridines undergo lithium 2,2,6,6-tetramethylpiperidide-induced N- to C-[1,2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-α,β-aziridinylphosphonates. The utility of this chemistry has been demonstrated in the asymmetric synthesis of a β-aminophosphonate.
摘要
N-膦酸酯末端氮丙啶在实验条件下容易发生锂 2,2,6,6-四甲基哌啶诱导的 N 到 C-[1,2]-膦酰基阴离子迁移，从而为合成有价值的反式-α,β-氮丙啶膦酸酯提供了一种立体控制的方法。该化学方法在β-氨基膦酸酯的不对称合成中得到了应用。
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