UNPRECEDENTED REARRANGEMENT REACTION OF 2-AZIRIDINEMETHANOLS WITH LOWER ORDER LITHIUM METHYLCYANOCUPRATE

被引：37

作者：

IBUKA, T

NAKAI, K

HABASHITA, H

FUJII, N

GARRIDO, F

MANN, A

CHOUNAN, Y

YAMAMOTO, Y

机构：

[1] CTR NEUROCHIM,CNRS,DEPT PHARMACOCHIM MOLEC,F-67084 STRASBOURG,FRANCE

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

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)60142-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

ComplementarY selectivity can be achieved in ring opening reactions of 2-aziridinemethanols by using either the Gilman reagent or lower order cyanocuprate. In the former case, the usual attack Of the Gilman reagent to the substrates 1 and 2 results in the formation of the expected ring opening products (3 and 4) and (7 and 8), respectively. In contrast, exposure of both 1 and 2 to the lower order cyanocuprate proceeds in an unprecedented fashion, presumably via epoxides D and G, to yield unexpected secondary alcohols (11 and 12) as the major products.

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页码：7421 / 7424

页数：4

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