REGIOSELECTIVE CARBOHYDROXYLATION OF ENOL ETHERS BY A PHOTOCYCLOADDITION-HYDROGENATION SEQUENCE

被引：24

作者：

BACH, T

机构：

[1] Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Orléansring 23

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)73179-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paterno-Buchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.

引用

页码：1855 / 1858

页数：4

共 14 条

[1]

[Anonymous], 1979, CATALYTIC HYDROGENAT

[2]

Arnold D. R., 1968, ADV PHOTOCHEM, V6, P301

[3] DIASTEREOMERICALLY PURE 3-(SILYLOXY)OXETANES BY A SELECTIVE PATERNO-BUCHI REACTION [J].