CYCLIZATIONS OF 5-SILYL-SUBSTITUTED 4,5-EPOXY-1-ALKANOLS - A CONFIGURATION DEPENDENT MODE OF RING-CLOSURE

被引：26

作者：

ADIWIDJAJA, G

FLORKE, H

KIRSCHNING, A

SCHAUMANN, E

机构：

[1] TECH UNIV CLAUSTHAL,INST ORGAN CHEM,D-38678 CLAUSTHAL ZELLERF,GERMANY

[2] UNIV HAMBURG,INST MINERAL PETROG,D-20146 HAMBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 48期

关键词：

D O I：

10.1016/0040-4039(95)01915-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation and proton-induced cyclization of silyl-substituted 4,5-epoxy-1-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group an the epoxy silane moiety is highly dependent on the configuration of the epoxy alcohols employed. Thus 1,4-anti epoxy alcohols exclusively yield tetrahydropyrans whereas the corresponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahydrofurans.

引用

页码：8771 / 8774

页数：4

共 17 条

[1]

ADIWIDJAJA G, 1995, LIEBIGS ANN, P501

[2]

BERTI G, 1984, J CHEM SOC PERK T 1, P1183, DOI 10.1039/p19840001183

[3] STUDY OF HYDROXYL PARTICIPATION IN ACYCLIC EPOXIDE SYSTEMS - ACID-CATALYZED REARRANGEMENTS OF TRANS-3,4-EPOXYPENTAN-1-OLS, AND CIS-3,4-EPOXYPENTAN-1-OLS, 4,5-EPOXYHEXAN-1-OLS, AND 5,6-EPOXYHEPTAN-1-OLS [J].