ASYMMETRIC-SYNTHESIS OF CHIRAL SPIROCYCLANES - SELECTIVE FORMATION OF 2-ACYLOXY-1-OXOSPIRO[4.N]ALKANES BY REGIOSELECTIVE AND STEREOSELECTIVE REARRANGEMENT OF ALPHA,BETA-EPOXY ACYLATES IN BICYCLO[N.3.0]ALKANE SYSTEMS

被引：30

作者：

FUJIOKA, H ^{[1
]}

KITAGAKI, S ^{[1
]}

IMAI, R ^{[1
]}

KONDO, M ^{[1
]}

OKAMOTO, S ^{[1
]}

YOSHIDA, Y ^{[1
]}

AKAI, S ^{[1
]}

KITA, Y ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 18期

关键词：

D O I：

10.1016/0040-4039(95)00517-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective formation of 2-acyloxy-1-oxospiro[4.n]alkanes by regio- and stereoselective rearrangement of alpha,beta-epoxy acylates in bicyclo[n.3.0]alkane systems has been achieved; the effect of the acyloxy group and stereochemistry of the starting epoxides were studied. The reaction was successfully applied to the synthesis of an optically active chiral spiro compound.

引用

页码：3219 / 3222

页数：4

共 28 条

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