Abstract
Abstract The use of enantiomerically pure sultams (+)-1 and (−)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α-bromopropanoate or α-bromobutanoate, the enolates of the corresponding N-acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.
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