CHEMISTRY OF 1-CHLOROALKYL ARYL SULFOXIDES - NEW METHODS FOR SYNTHESIZING CARBONYL-COMPOUNDS AND THEIR USE IN ASYMMETRIC-SYNTHESIS

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, alpha-substituted carbonyl compounds, vinyl- and divinyl ketones, 1-acylbutadienes, alpha,beta-unsaturated carbonyl compounds, aldols, epoxides, allylic alcohols, (Z)-N-arylaziridines, and alpha-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, alpha-amino aldehydes, and alpha-hydroxycarboxylic acids and their derivatives were synthesized from carbonyl compounds or imines and the optically active 1-chloroalkyl p-tolyl sulfoxides.