TRICYCLIC OXONIUM-DIRECTED ADDITION - REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE IODINATION REACTIONS IN 2,3-EPOXY CYCLOOCT-5-EN-1-OLS AND 2,3-EPOXY-5-EN-1-ONE

被引：8

作者：

ALVAREZ, E

DIAZ, MT

RODRIGUEZ, ML

MARTIN, JD

机构：

[1] Centro de Productos Naturales Orgánicos Antonio González, Universidad de La Laguna-C.S.I.C., Teneriffe, Ctra. La Esperanza 2

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 11期

关键词：

D O I：

10.1016/0040-4039(90)80035-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transannular O-heterocyclization of 9-oxabicyclo[6.1.0] non-4-en-2-ols and 9-oxabicyclo[6.1.0] non-4-en-2-one by iodine-assisted oxirane ring expansion was studied. The stereo- and regioselectivity for the[4.2.1] vs[3.3.1] 10-oxabicyclo nonane skeletons are studied in terms of a tricyclic oxonium ion intermediate and rationalized by means of MNDO calculations. © 1990.

引用

页码：1629 / 1632

页数：4

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