STEREOSELECTIVE SUBSTITUTION IN 2-BROMO AMIDES IN THE PRESENCE OF AG+OR AG2O

Citation
F. Dangeli et al., STEREOSELECTIVE SUBSTITUTION IN 2-BROMO AMIDES IN THE PRESENCE OF AG+OR AG2O, Journal of organic chemistry, 60(13), 1995, pp. 4013-4016
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
60
Issue
13
Year of publication
1995
Pages
4013 - 4016
Database
ISI
SICI code
0022-3263(1995)60:13<4013:SSI2AI>2.0.ZU;2-L
Abstract
Bromine displacement by a primary, secondary, or tertiary amine, or me thanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with hig h yields and stereo selectivity. Soluble Ag+ promotes inversion, and s olid Ag2O promotes retention of configuration. However, in the case of Et(3)N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbut anamide 5, the displacement by a primary or secondary amine or methano l occurs only in the presence of Ag2O, possibly with retention of conf iguration.