CATALYTIC ASYMMETRIC-SYNTHESIS OF SECONDARY ALCOHOLS USING CHIRAL IS-1-AMINO-2-HYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE AS CHIRAL LIGAND

Authors
BELLUCCI CM BERGAMINI A COZZI PG PAPA A TAGLIAVINI E UMANIRONCHI A
Citation
Cm. Bellucci et al., CATALYTIC ASYMMETRIC-SYNTHESIS OF SECONDARY ALCOHOLS USING CHIRAL IS-1-AMINO-2-HYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE AS CHIRAL LIGAND, Tetrahedron : asymmetry, 8(6), 1997, pp. 895-902
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
6
Year of publication
1997
Pages
895 - 902
Database
ISI
SICI code
0957-4166(1997)8:6<895:CAOSAU>2.0.ZU;2-P
Abstract
The synthesis and resolution of is-1-amino-2-hydroxy-1,2,3,4-tetrahydr onaphthalene 5 by a simple and straightforward methodology has been ac hieved. The homochiral aminoalcohol has been used in the catalytic red uction of ketones by means of BH3 . SMe(2) affording secondary alcohol s in high enantiomeric excesses. On the contrary low enantiomeric exce sses have been obtained when N,N-dibutyl-1-amino-2-hydroxytetrahydrona phthalene 11 has been used to catalyze the enantioselective addition o f Et(2)Zn to benzaldehyde. (C) 1997 Elsevier Science Ltd.