α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines.

Journal article

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.

Authors: Hodgson, D; Xu, Z

• Publication status: Published
• Journal: Beilstein journal of organic chemistry
• Volume: 6
• Pages: 978-983
• Publication date: 2010-01-01
• DOI: 10.3762/bjoc.6.110
• EISSN: 1860-5397
• ISSN: 1860-5397
• Language: English
• Keywords: synthetic methods; amino acids; lithiation; migration; aziridines