Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidine derived from (1S, 2S, 3R, 4R)-3-amino-7, 7-dimethoxynorbornan-2-ol. An efficient …

AAM Lapis, Â de Fátima, JED Martins, VEU Costa…

Index: Lapis, Alexandre A. M.; De Fatima, Angelo; Martins, Jose E. D.; Costa, Valentim E. U.; Pilli, Ronaldo A. Tetrahedron Letters, 2005 , vol. 46, # 3 p. 495 - 498

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Citation Number: 37

Abstract

Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst prepared in situ from (1S, 2S, 3R, 4R)-3-amino-7, 7- dimethoxynorbornan-2-ol (). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43–95%) and good yields (75– 94%), except for ketones bearing electron-withdrawing groups. The methodology was ...