Ring-enlarging cyclohexane annulations

被引：35

作者：

Ando, S ^{[1
]}

Minor, KP ^{[1
]}

Overman, LE ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92697

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期

关键词：

D O I：

10.1021/jo970399i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Prins-pinacol rearrangement is the key step in a new method for synthesizing cis-bicyclo[n.4.0]alkanones. The alkenyl acetal rearrangement substrates 1 are assembled from cycloalkanone precursors in four steps (Table 1). Prins-pinacol rearrangement to form cis-bicyclo[n.4.0]alkanones 3 is best accomplished by exposure of 1 to 1 equiv of TMSOTf and a proton scavenger (2,6-di-tert-butyl-4-methylpyridine) at -78 degrees C --> rt.

引用

收藏

页码：6379 / 6387

页数：9

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