Tetrahedron: Asymmetry

Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones

E Brown, A Lézé, J Touet

Index: Brown, Eric; Leze, Antoine; Touet, Joel Tetrahedron Asymmetry, 1996 , vol. 7, # 7 p. 2029 - 2040

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Citation Number: 9

Abstract

LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(−)-2-(2-isoindolinyl) butan-1-ol 1 reduced the six α-aminophenones 4–9 into the corresponding optically active β- aminoalcohols 10–15 whose ee's were in the range 40–97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(−)- ...