Abstract

Abstract The influence of LiCl on deprotonation of 2- tert -butyl-2-methyl-1,3-dioxan-5-one 1 and tropinone 8 with chiral lithium amide bases is described. In most cases the enantioselectivity was much higher in the presence of 1 (or more) equivalent(s) of LiCl. In an extreme case the opposite enantiomers were obtained in the presence and in the absence of LiCl. The magnitude of LiCl effects and the optimal amount of LiCl varied with the ketone - lithium amide system. A new deprotonation procedure which utilizes the amine hydrochloride for generation of the chiral lithium amide is described. The effects of other lithium salts including LiBr, LiI, LiClO 4 were also briefly examined.

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