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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Reaction of Silyllithium, α-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of α-Substituted β-(Silyloxy)-α-hydroxy Acid Derivatives.
Journal of Organic Chemistry 2017 October 7
A single-flask reaction of silyllithium, α-keto N-tert-butanesulfinyl imidates and aldehydes has been developed for the diastereoselective synthesis of α,β-dihydroxy acid derivatives. In this reaction, the nucleophilic addition of silyllithium to chiral α-keto imidates followed by silyl migration forms chiral aza-enolates, which react diastereoselectively with aldehydes. Subsequent [1,4]-O → O silyl migration affords α-substituted β-(silyoxy)-α-hydroxy imidates.
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