Tetrahedron Letters

(+)-1 (S), 5 (R), 8 (S)-8-phenyl-2-azabicyclo [3.3. 0] octan-8-ol n, o-methylboronate (2) and its enantiomer, chiral chemzymes which serve as catalysts for their own …

EJ Corey, CP Chen, GA Reichard

Index: Corey, E. J.; Chen, C.-P.; Reichard, Gregory A. Tetrahedron Letters, 1989 , vol. 30, # 41 p. 5547 - 5550

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Citation Number: 92

Abstract

Abstract An efficient synthesis of (+)-1 (S), 5 (R), 8 (S)-8-phenyl-2-azabicyclo [3.3. 0] octan-8- ol (1) and its enantiomer is described. The B-methyloxazaborolidine derivatives (2) of these amino alcohols are excellent catalysts (chemzymes) for the enantioselective reduction of a variety of achiral ketones to chiral secondary alcohols, eg acetophenone, 98% ee; pinacolone, 98% ee; α-tetralone, 97% ee; and 2-bromo-2-cyclohexen-1-one, 98% ee. The ...