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
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.
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页码:6379 / 6387
页数:9
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