Tetrahedron: Asymmetry

New chiral phosphorus catalysts derived from (S)-binaphthol for highly enantioselective reduction of acetophenone by borane

MFP Ma, K Li, Z Zhou, C Tang, ASC Chan

Index: Ma, Margaret F. P.; Li, Kangying; Zhou, Zhenghong; Tang, Chuchi; Chan, Albert S. C. Tetrahedron Asymmetry, 1999 , vol. 10, # 17 p. 3259 - 3261

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Citation Number: 19

Abstract

New chiral (+)-2, 2′-O, O-(1, 1′-binaphthyl)-dioxo-N, N-diethylphospholidine 1 and its borane complex 3 were prepared from (S)-binaphthol and their use as catalysts in enantioselective borane reductions of prochiral acetophenone were investigated. Enantiomeric excesses of up to 98.5% have been obtained using 6 mol% of 1 at room temperature and using 6 mol% of 3 at 100° C.