Addition–Rearrangement of Ketenes with Lithium N-tert-Butanesulfinamides: Enantioselective Synthesis of α,α-Disubstituted α‑Hydroxycarboxylic Acid Derivatives

Addition of the lithium salts of chiral N-substituted tert-butanesulfinamides to ketenes and subsequent silylation initiates stereoselective [2,3]-rearrangement, which affords enantioenriched α,α-disubstituted α-sulfenyloxy carboxamides through a reaction that faithfully transfers the absolute stere...

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Bibliographic Details
Published in:Organic letters 2019-06, Vol.21 (12), p.4671-4675
Main Authors: Ma, Peng-Ju, Tang, Fan, Yao, Yun, Lu, Chong-Dao
Format: Article
Language:English
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Summary:Addition of the lithium salts of chiral N-substituted tert-butanesulfinamides to ketenes and subsequent silylation initiates stereoselective [2,3]-rearrangement, which affords enantioenriched α,α-disubstituted α-sulfenyloxy carboxamides through a reaction that faithfully transfers the absolute stereochemistry of the lithiated sulfinylamides to the α-carbon of the amide products. This addition–rearrangement can be performed together with ketene formation from acyl chloride in a single flask, providing a new and practical synthetic route to α-hydroxycarboxylic acid derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01555