Chiral acetals as stereoinductors: Diastereoface selective alkylation of dihydrobenzoxazine-derived amide enolates

Authors
Mulzer, J Langer, O Hiersemann, M Bats, JW Buschmann, J Luger, P
Citation
J. Mulzer et al., Chiral acetals as stereoinductors: Diastereoface selective alkylation of dihydrobenzoxazine-derived amide enolates, J ORG CHEM, 65(20), 2000, pp. 6540-6546
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
20
Year of publication
2000
Pages
6540 - 6546
Database
ISI
SICI code
0022-3263(20001006)65:20<6540:CAASDS>2.0.ZU;2-5
Abstract
Novel dihydrobenzoxazine-derived acetals of type 3 have been developed for asymmetric C-alkylations of propionyl amide enolates. High stereoselectivit ies are obtained for amides 15 and 22 which are rationalized in terms of in tramolecular metal chelate formation.