ORGANOALUMINUM-PROMOTED CYCLOADDITION OF TRIALKYLSILYLKETENE WITH ALDEHYDES - A NEW, STEREOSELECTIVE APPROACH TO CIS-2-OXETANONES AND 2(Z)-ALKENOIC ACIDS

被引:38
作者
CONCEPCION, AB [1 ]
MARUOKA, K [1 ]
YAMAMOTO, H [1 ]
机构
[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN
关键词
D O I
10.1016/0040-4020(95)00142-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) can be successfully utilized as a highly efficient Lewis acid for achieving high stereoselectivity in the cycloaddition of trialkylsilylketene with aldehydes. This method serves as a highly effective route to the synthesis of cis-2-oxetanones from saturated aldehydes, and the synthesis of 2(Z)-alkenoic acids from aromatic and alpha,beta-unsaturated aldehydes.
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页码:4011 / 4020
页数:10
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