Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds

被引：18

作者：

Hanaki, N ^{[1
]}

Ishihara, K ^{[1
]}

Kaino, M ^{[1
]}

Naruse, Y ^{[1
]}

Yamamoto, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,NAGOYA,AICHI 46401,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 21期

关键词：

D O I：

10.1016/0040-4020(96)00253-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo[n.4.0]alkane, 2-oxabicyclo[n.4.0]alk-1(6)-ene and 2-oxabicyclo[n.4.0]alk-1(6+n)-ene is stereoselectively synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent and tertiaryamine). These compounds lead to polyfunctionalized cyclic compounds and some natural products. We propose that this annulation reaction proceeds through a pure S(N)2-like mechanism. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7297 / 7320

页数：24

共 34 条

[31] A One-Pot Process toward 2-Hydroxy-1,3-diamino Compounds: A Synthetic Application to Dual Norepinephrine/Serotonin Reuptake Inhibitors
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