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
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.
引用
收藏
页码:2179 / 2182
页数:4
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