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

Authors
Bataille, P Paterne, M Brown, E
Citation
P. Bataille et al., Further enantioselective syntheses of alpha-arylalkanamines via intermediate addition of Grignard reagents to a chiral hydrazone derived from (R)-(-)-2-aminobutan-1-ol, TETRAHEDR-A, 10(8), 1999, pp. 1579-1588
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
8
Year of publication
1999
Pages
1579 - 1588
Database
ISI
SICI code
0957-4166(19990423)10:8<1579:FESOAV>2.0.ZU;2-O
Abstract
Reaction of various aromatic aldehydes with the chiral hydrazine (R)-(-)-2, derived from 2-aminobutan-1-ol (R)-(-)-1, gave the corresponding hydrazone s 5-12. Enantioselective addition of EtMgBr or n-BuMgBr to 5-8 gave the tri substituted 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 enantiom erically enriched alpha-arylalkanamines (R)-(+)-14a-f (e.e.s=90-93%). (C) 1 999 Elsevier Science Ltd. All rights reserved.