TOSYLATED LITHIUM 2-(LITHIOMETHYL)-2-PROPEN-1-OLATE - A GAMMA-ALKOXIDE ALLYL SULFONE ANION IN ORGANIC-SYNTHESIS

Dilithiated 2-(tosylmethyl)-2-propen-1-ol (6) functioned as a nucleoph ile at the alpha-position of the allylic anion in reactions with deute rium oxide, alkyl halides, and aldehydes, and in conjugate additions t o alpha,beta-unsaturated carbonyl compounds. With nitro-olefins conjug ate addition occurred at the gamma-position of the allylic anion. The hydroxy ester derived by reaction with tert-butyl bromoacetate was con verted into a variety of synthetically useful dienic and beta,gamma-un saturated delta-lactones. The reductive detosylation of some of the hy droxy sulfones with sodium amalgam was also studied.