Tetrahedron: Asymmetry

Enantioselective syntheses of α-phenylalkanamines via intermediate addition of Grignard reagents to chiral hydrazones derived from (R)-(−)-2-aminobutan-1-ol

P Bataille, M Paterne, E Brown

Index: Bataille, Patricia; Paterne, Michel; Brown, Eric Tetrahedron Asymmetry, 1998 , vol. 9, # 12 p. 2181 - 2192

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Citation Number: 28

Abstract

The hydrazine (R)-(−)-28 was obtained in four steps from 2-aminobutan-1-ol (R)-(−)-11, and reacted with benzaldehyde to give the hydrazone (R)-(−)-29. Nucleophilic addition of various alkyl Grignard reagents to the latter yielded the corresponding trisubstituted hydrazines (R, R)-30a–g in 70–89% yields and having des= 100%(1H and 13C NMR). Catalytic hydrogenolysis of these hydrazines afforded the corresponding (R)-(+)-α- ...