1-クロロアルキルアリルスルホキシドの化学 : カルボニル化合物の新規合成法の開拓と不斉合成への展開

Abstract

This review deals with novel methods for a homologation of carbonyl compounds by using 1-chloroalkyl aryl sulfoxides as acyl anion equivalents. The products obtained from these methods are those of dialkyl ketones, aldehydes, α-substituted carbonyl compounds, vinyl-and divinyl ketones, 1-acylbutadienes, α, β-unsaturated carbonyl compounds, aldols, epoxides, allylic alcohols, (Z)-N-arylaziridines, and α-hydroxycarboxylic acids and their derivatives. Novel synthetic methods for cyclic ketones or new annulation procedures were achieved by using these new procedures. As the novel methods for asymmetric synthesis, a practical procedure for preparing optically pure 1-chloroalkyl p-tolyl sulfoxides was achieved. Optically active epoxides, (Z)-N-arylaziridines, α-amino aldehydes, and α-hydroxycarboxylic acids and their derivatives were synthesized from carbonyl compounds or imines and the optically active 1-chloroalkyl p-tolyl sulfoxides.