REGIOSELECTIVE AND STEREOSPECIFIC FORMATION OF 2-ETHYNYL-3-HYDROXYTETRAHYDROPYRAN DERIVATIVES VIA 6-ENDO RING-CLOSURE

被引：66

作者：

MUKAI, C ^{[1
]}

IKEDA, Y ^{[1
]}

SUGIMOTO, Y ^{[1
]}

HANAOKA, M ^{[1
]}

机构：

[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA 920,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(00)76790-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient access to tetrahydropyran derivatives via highly regio- and stereoselective 6-endo tet mode ring opening of an epoxide by an internal hydroxy group has been developed Cobalt complexes, derived from trans-4,5-epoxy-heptyn-1-ols and dicobalt octacarbonyl were treated with a catalytic amount of BF3.OEt(2) in CH2Cl2 at -78 degrees C to afford cis-2-ethynyl-3-hydroxytetrahydropyran derivatives in a highly regio- and stereoselective manner. Similar treatment of cis-4,5-epoxides provided the corresponding trans-tetrahydropyrans selectively.

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页码：2179 / 2182

页数：4

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