Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates

Authors
Palacios, F de Retana, AMO Gil, JI
Citation
F. Palacios et al., Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates, TETRAHEDR L, 41(28), 2000, pp. 5363-5366
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
28
Year of publication
2000
Pages
5363 - 5366
Database
ISI
SICI code
0040-4039(20000708)41:28<5363:EAESOE>2.0.ZU;2-T
Abstract
An efficient synthesis of 2H-azirines substituted with a phosphonate group is described. The key step is an alkaloid-mediated Neber reaction of beta-k etoxime tosylates. Reduction of 2H-azirines with sodium borohydride in etha nol gives 2-phosphorylated cis-aziridines. (C) 2000 Published by Elsevier S cience Ltd.