Kinetic resolution of racemic. beta.-hydroxy amines by enantioselective N-oxide formation

…, LDL Lu, SM Viti, KB Sharpless

Index: Miyano, Sotaro; Lu, Linda D.-L.; Viti, Steven M.; Sharpless, K. Barry Journal of Organic Chemistry, 1985 , vol. 50, # 22 p. 4350 - 4360

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Citation Number: 107

Abstract

A practical and fairly general procedure for the kinetic resolution of@-hydroxy tertiary amines is described. It involves the selective oxidation of one enantiomer to the N-oxide by using tert-butyl hydroperoxide (TBHP) and a chiral catalyst prepared by mixing 2 parts of titanium isopropoxide (Ti (Oi-Pr) & and 1.2 parts of either (+)-or (-)-diisopropyl tartrate (DIPT). The product N-oxide and the unreacted amino alcohol are then easily separated by ...