Nucleophilic alkenoylation of aldehydes with metalated alpha-aminonitriles: regioselective synthesis of alpha-hydroxyenones

Authors
Pierre, F Enders, D
Citation
F. Pierre et D. Enders, Nucleophilic alkenoylation of aldehydes with metalated alpha-aminonitriles: regioselective synthesis of alpha-hydroxyenones, TETRAHEDR L, 40(29), 1999, pp. 5301-5305
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5301 - 5305
Database
ISI
SICI code
0040-4039(19990716)40:29<5301:NAOAWM>2.0.ZU;2-U
Abstract
An efficient regioselective two-step synthesis of alpha-hydroxyenones 3a-p is reported. The methodology involves nucleophilic addition of metalated be ta,gamma-unsaturated-alpha-aminonitriles to aldehydes, followed by a mild s ilver nitrate induced hydrolysis of the aminonitrile adducts to afford the title compounds in overall yields of 61-83%. (C) 1999 Elsevier Science Ltd. All rights reserved.