The Mn(Salen)-catalyzed oxidative kinetic resolution of secondary alcohols: reaction development and scope

A series of chiral Mn(Salen) complexes have been synthesized and submitted to the kinetic resolution of secondary alcohols bearing a large hindrance in the biphasic system, which is composed of water and CH2Cl2. After evaluating the appropriate complex, additive, and other conditions, chiral secondary alcohols were obtained with enantiomeric excesses of up to 98.6% in 6 min.

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(R,R)-N,N′-Bis(5-tert-butyl-salicylidene)-1,2-cyclohexanediamineC28H38N2O2[α]D20=-206 (c 0.0142, CH2Cl2)Absolute configuration: (R,R)Source of chirality: l-Tartaric acid resolution