A practical method for the acylation of 2-imidazolidinone and 2-oxazolidinone chiral auxiliaries with 2-bromoacyl halides

Authors
Candeias, SX Jenkins, K Ribeiro, ASC Afonso, CAM Caddick, S
Citation
Sx. Candeias et al., A practical method for the acylation of 2-imidazolidinone and 2-oxazolidinone chiral auxiliaries with 2-bromoacyl halides, SYN COMMUN, 31(21), 2001, pp. 3241-3254
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
21
Year of publication
2001
Pages
3241 - 3254
Database
ISI
SICI code
0039-7911(2001)31:21<3241:APMFTA>2.0.ZU;2-3
Abstract
Optimised conditions for the acylation of (S)-4-(1-methylethyl) -oxazolidin -2-one 4, (R)-4-phenyloxazolidin-2-one 5 and 4-(R), (5S)-1,5-dimethyl-4-phe nylimidazolidin-2-one 3 with 2-bromoacyl halides were developed. For imidaz olidin-2-one 3 the optimum conditions require the use of the hindered bases 2,6-di-t-butylpyridine or 2,6-lutidine in order to reduce the ketene format ion which has a strong preference for O-acylation.