A ONE-POT AZA-PAYNE REARRANGEMENT-EPOXIDE RING-OPENING REACTION OF 2-AZIRIDINEMETHANOLS - A REGIOSELECTIVE AND STEREOSELECTIVE SYNTHETIC ROUTE TO DIASTEREOMERICALLY PURE 1,2-AMINO ALCOHOLS

Authors
NAKAI K IBUKA T OTAKA A TAMAMURA H FUJII N YAMAMOTO Y
Citation
K. Nakai et al., A ONE-POT AZA-PAYNE REARRANGEMENT-EPOXIDE RING-OPENING REACTION OF 2-AZIRIDINEMETHANOLS - A REGIOSELECTIVE AND STEREOSELECTIVE SYNTHETIC ROUTE TO DIASTEREOMERICALLY PURE 1,2-AMINO ALCOHOLS, Tetrahedron letters, 36(35), 1995, pp. 6247-6250
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
35
Year of publication
1995
Pages
6247 - 6250
Database
ISI
SICI code
0040-4039(1995)36:35<6247:AOARRR>2.0.ZU;2-V
Abstract
A regio- and stereoselective synthetic route to diastereomerically pur e 1,2-amino alcohols via a one-pot aza-Payne rearrangement - epoxide r ing opening reaction of 2-aziridinemethanols is reported. Satisfactory yields are obtained in excellent diastereoisomeric excesses by succes sive exposure of 2-aziridinemethanols to potassium hydride and nucleop hilic reagents in a one-pot manner.