Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes

Authors
Capriati, V Florio, S Luisi, R
Citation
V. Capriati et al., Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes, EUR J ORG C, (11), 2001, pp. 2035-2039
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
2001
Pages
2035 - 2039
Database
ISI
SICI code
1434-193X(200106):11<2035:AO2-AH>2.0.ZU;2-E
Abstract
The oxazoline-derived titanium azaenolate 6 couples highly stereoselectivel y with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very p oor or no stereoselectivity. Lithium, aluminum and tin azaenolates have als o been shortly studied.