Kinetic Resolution of Racemic Carboxylic Acids by an L-Histidine-Derived Sulfonamide-Induced Enantioselective Esterification Reaction.

[摘要]：The direct and catalytic kinetic resoln. of racemic carboxylic acids bearing a Bronsted base such as O-protected a-hydroxy carboxylic acids R1OCHR2CO2H (R1 = pyrrolidin-1-ylcarbonyl; R2 = Me2CH, Ph, PhCH2, Me3CSiPh2) and N-protected a-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-Bu alc. for the first time. Highly asym. induction [S(kfast/kslow) = up to 56] has been achieved under the equil. between a chiral catalyst and two diastereomeric acylammonium salts through an intramol. hydrogen-bonding interaction.

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