ORGANOALUMINUM-PROMOTED CYCLOADDITION OF TRIALKYLSILYLKETENE WITH ALDEHYDES - A NEW, STEREOSELECTIVE APPROACH TO CIS-2-OXETANONES AND 2(Z)-ALKENOIC ACIDS
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CONCEPCION, AB
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NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPANNAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN
CONCEPCION, AB
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MARUOKA, K
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NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPANNAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN
MARUOKA, K
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YAMAMOTO, H
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NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPANNAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN
YAMAMOTO, H
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[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA,AICHI 46401,JAPAN
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.