UNEXPECTED SELECTIVITY BETWEEN PINACOLIC REARRANGEMENT AND INTRAMOLECULAR DISPLACEMENT IN THE ACID-PROMOTED EPOXIDE RING-OPENING OF 6-EXO-CYANO-3,8-DIOXABICYCLO[3.2.1.0(2,4)]OCT-6-ENDO-YL ESTERS

被引：11

作者：

ALLEMANN, S ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)86963-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid promoted epoxide ring opening of 2-exo-cyano-5-exo,6-exo-epohy-7-oxa-bicyclo[2.2.1]hept-2-endo-yl acetate is accompanied by a Wagnet-Meerwein (pinacolic) rearrangemant when run in CH2Cl2/HSO3-F and by endo acetoxy group participation when run in CF3CH(OH)CF3/HClO4. An efficient and stereoselective trans-double hydroxylation of centers C(5) and C(6) of the ''naked sugar'' (1R,2S,4R)-2-exo-cyano-7-oxabicyclo[2.2.1]hept-2-endo-yl (1S')-camphanate is also presented.

引用

页码：2469 / 2478

页数：10

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