One-pot highly stereoselective reduction of beta-keto amides to syn-gamma-aminols

Authors
Bartoli, G Bosco, M Dalpozzo, R Marcantoni, E Massaccesi, M Rinaldi, S Sambri, L
Citation
G. Bartoli et al., One-pot highly stereoselective reduction of beta-keto amides to syn-gamma-aminols, TETRAHEDR L, 42(50), 2001, pp. 8811-8815
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
50
Year of publication
2001
Pages
8811 - 8815
Database
ISI
SICI code
0040-4039(200112)42:50<8811:OHSROB>2.0.ZU;2-H
Abstract
In the presence of titanium tetrachloride, the borane/tetrahydrofuran compl ex can reduce 2-methyl-3-oxoamides into the corresponding syn-aminols in go od yields and high diastereoselectivity. The use of borane/dimethyl sulfide instead of BH3/THF allows a partial reduction to syn-beta -hydroxyamides. (C) 2001 Elsevier Science Ltd. All rights reserved.