Further enantioselective syntheses of α-arylalkanamines via intermediate addition of Grignard reagents to a chiral hydrazone derived from (R)-(-)-2-aminobutan-1-ol

被引：9

作者：

Bataille, P ^{[1
]}

Paterne, M ^{[1
]}

Brown, E ^{[1
]}

机构：

[1] Fac Sci, Organ Synth Lab, CNRS, ESA 6011, F-75085 Le Mans 9, France

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(99)00146-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of various aromatic aldehydes with the chiral hydrazine (R)-(-)-2, derived from 2-aminobutan-1-ol (R)-(-)-1, gave the corresponding hydrazones 5-12. Enantioselective addition of EtMgBr or n-BuMgBr to 5-8 gave the trisubstituted hydrazines 13a-f (d.e.s=100%). Catalytic hydrogenolysis (6 bar/Pd-C/110 degrees C/5 h) of the N-N bond of the latter afforded the enantiomerically enriched alpha-arylalkanamines (R)-(+)-14a-f (e.e.s=90-93%). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1579 / 1588

页数：10

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