Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline

Authors
Florio, S Capriati, V Luisi, R
Citation
S. Florio et al., Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline, TETRAHEDR L, 41(27), 2000, pp. 5295-5298
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
27
Year of publication
2000
Pages
5295 - 5298
Database
ISI
SICI code
0040-4039(20000701)41:27<5295:HSSOOA>2.0.ZU;2-X
Abstract
Boron and titanium azaenolates 2 and 4, generated at 0 degrees C and -100 d egrees C, respectively, from the optically active chloromethyloxazoline 1, have been found to couple with aliphatic ketones in a highly diastereoselec tive fashion ending up with the formation of optically active oxazolinyl ox iranes 3. Less stereoselective was the reaction with aromatic ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.