Abstract
Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2- syn selectivity while 2-methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.
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