Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Beilstein J Org Chem. 2010 Oct 13;6:978-83. doi: 10.3762/bjoc.6.110.
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.
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。
