ENANTIOSELECTIVE SYNTHESIS OF 1,2-AMINOALCOHOL, 1,3-AMINOALCOHOL AND 1,4-AMINOALCOHOL BY THE ADDITION OF DIALKYLZINCS TO 1,2-AMINOALDEHYDE,1,3-AMINOALDEHYDE AND 1,4-AMINOALDEHYDE

Authors
LUTZ C LUTZ V KNOCHEL P
Citation
C. Lutz et al., ENANTIOSELECTIVE SYNTHESIS OF 1,2-AMINOALCOHOL, 1,3-AMINOALCOHOL AND 1,4-AMINOALCOHOL BY THE ADDITION OF DIALKYLZINCS TO 1,2-AMINOALDEHYDE,1,3-AMINOALDEHYDE AND 1,4-AMINOALDEHYDE, Tetrahedron, 54(23), 1998, pp. 6385-6402
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
23
Year of publication
1998
Pages
6385 - 6402
Database
ISI
SICI code
0040-4020(1998)54:23<6385:ESO11A>2.0.ZU;2-3
Abstract
Chiral 1,3- and 1,4-aminoalcohols were prepared by the addition of fun ctionalized dialkylzincs to 1,3-aliphatic and 1,4-unsaturated aminoald ehydes with good to excellent enantioselectivity. Syn- or anti-1,2-ami noalcohols are stereoselectively obtained by asymmetric addition of di alkylzincs to alpha-aminoaldehydes depending on the choice of the chir al catalyst. A chelate controlled addition is observed if less than st oichiometric amounts of Ti(Oi-Pr)(4) are used. (C) 1998 Elsevier Scien ce Ltd. All rights reserved.