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

被引：17

作者：

NAKAI, K

IBUKA, T

OTAKA, A

TAMAMURA, H

FUJII, N

YAMAMOTO, Y

机构：

[1] KYOTO UNIV,FAC PHARMACEUT SCI,SAKYO KU,KYOTO 60601,JAPAN

[2] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01203-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols via a one-pot aza-Payne rearrangement - epoxide ring opening reaction of 2-aziridinemethanols is reported. Satisfactory yields are obtained in excellent diastereoisomeric excesses by successive exposure of 2-aziridinemethanols to potassium hydride and nucleophilic reagents in a one-pot manner.

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页码：6247 / 6250

页数：4

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