Photocyclization reactions of cyclohexa- and cyclopenta-fused pyridinium salts. Factors governing regioselectivity

被引：18

作者：

Zhao, ZM ^{[1
]}

Duesler, E ^{[1
]}

Wang, CH ^{[1
]}

Guo, H ^{[1
]}

Mariano, PS ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 21期

关键词：

D O I：

10.1021/jo051348l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The results of studies described in this report show that irradiation of 1,2-cyclopenta-fused pyridinium perchlorate in aqueous base promotes a remarkably regioselective photocyclization reaction that results in exclusive formation of a single tricyclic allylic alcohol. Moreover, transformation of this photoproduct to a spirocyclic amido diester followed by enzymatic desymmetrization produces an enantiomerically pure monoalcohol. This chemistry comprises a highly concise sequence for the preparation of what should become a useful synthon in synthetic organic chemistry.

引用

页码：8508 / 8512

页数：5