From overstoichiometric to substoichiometric enantioselective protonation with 2-sulfinyl alcohols: A view in perspective

A detailed study of the deracemization of pipecolic acid amides is reported. Enantioselective protonation of the lithium enolates of these amides with use of commercially available ephedrines led to enantiomeric excesses (ee values) higher than 99 %. The success of the reaction was strongly dependent on the following parameters: the base, the reaction temperature, the structure of the chiral source, and the achiral quenching reagent. sBuLi and the bimetallic base "potassium alkoxide/nBuLi" were the only bases to allow complete formation of the enolate in conjunction with high stereocontrol of the protonation. Experiments with (+)-or (-)-ephedrine derivatives as chiral sources and deuteriated

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From overstoichiometric to substoichiometric enantioselective protonation with 2-sulfinyl alcohols: A view in perspective

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References 3 publications

From Overstoichiometric to Substoichiometric Enantioselective Protonation with 2‐Sulfinyl Alcohols: A View in Perspective

From Overstoichiometric to Substoichiometric Enantioselective Protonation with 2‐Sulfinyl Alcohols: A View in Perspective

Efficient Deracemization of Pipecolic Acid Amides through Enantioselective Protonation of Their Lithium Enolates: Insights into the Origin of the Transferred Proton

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