Synthetic routes to allenic acids and esters and their stereospecific conversion to butenolides

JA Marshall, MA Wolf, EM Wallace

文献索引：Marshall, James A.; Wolf, Mark A.; Wallace, Eli M. Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 367 - 371

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被引用次数: 166

摘要

The synthesis of allenic acids and esters and their conversion to butenolides has been examined in some detail. Racemic butenolides 10 are efficiently prepared from the esters 8 through treatment with BCl3 and exposure of the derived acid 9 to catalytic AgNO3 in acetone. Conversion of the enantioenriched allenylstannane (S)-17 to the acid 18 through lithiation and subsequent carboxylation with CO2 afforded racemic product. The ...