Novel route to functionalized cyclooctanoids via [5+3] cycloaddition

被引：13

作者：

Krishna, UM ^{[1
]}

Deodhar, KD ^{[1
]}

Trivedi, GK ^{[1
]}

Mobin, SM ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Natl Single Crystal Xray Diffract Facil, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 03期

关键词：

D O I：

10.1021/jo0353583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclo-octanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crystal X-ray analysis. It is noteworthy that the hydrogenation of 3 in ethanol solvent gave the transannulated product 5, whereas the expected dihydro product 4 was obtained when the reaction was run in nonnucleophilic solvents. The mechanistic pathway is discussed.

引用

页码：967 / 969

页数：3

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