Enantioselective synthesis of 3-hydroxypiperidin-2-ones

Authors
Gibbs, G Hateley, MJ McLaren, L Welham, M Willis, CL
Citation
G. Gibbs et al., Enantioselective synthesis of 3-hydroxypiperidin-2-ones, TETRAHEDR L, 40(5), 1999, pp. 1069-1072
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
1069 - 1072
Database
ISI
SICI code
0040-4039(19990129)40:5<1069:ESO3>2.0.ZU;2-W
Abstract
An efficient synthesis of (S)- and (R)-3-hydroxypiperidin-2-ones from methy l 5-nitro-2-oxopentanoate is described. A one-pot enzyme catalysed hydrolys is of the eater and reduction of the ketone gave enantiopure 2-hydroxy-5-ni tropentanoic acids which on esterification, catalytic hydrogenation over a platinum(IV) oxide catalyst and intramolecular cyclisation gave the target compounds in 93% overall yield and >99% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.