Conformational control in the SuperQuat chiral auxiliary 5,5-dimethyl-4-iso-propyloxazolidin-2-one induces the iso-propyl group to mimic a tert-butylgroup

Authors
Bull, SD Davies, SG Key, MS Nicholson, RL Savory, ED
Citation
Sd. Bull et al., Conformational control in the SuperQuat chiral auxiliary 5,5-dimethyl-4-iso-propyloxazolidin-2-one induces the iso-propyl group to mimic a tert-butylgroup, CHEM COMMUN, (18), 2000, pp. 1721-1722
Citations number
12
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
18
Year of publication
2000
Pages
1721 - 1722
Database
ISI
SICI code
1359-7345(2000):18<1721:CCITSC>2.0.ZU;2-F
Abstract
H-1 NMR nOe spectroscopic studies reveal that conformational control in the enolates of N-acyl-5,5-dimethyl-4-iso-propyloxazolidin-2-ones ensures that the stereodirecting effect of its 4-iso-propyl-5,5-dimethyl functional gro up affords superior levels of facial selectivity normally associated with e nolates derived from N-acyl-4-tert-butyloxazolidin-2-ones.