First asymmetric synthesis of a 6-alkoxy-5,6-dihydro-1,3-oxazine: A promising enantioselective route to beta-amido aldehydes

Authors
Gizecki, P Dhal, R Toupet, L Dujardin, G
Citation
P. Gizecki et al., First asymmetric synthesis of a 6-alkoxy-5,6-dihydro-1,3-oxazine: A promising enantioselective route to beta-amido aldehydes, ORG LETT, 2(5), 2000, pp. 585-588
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
5
Year of publication
2000
Pages
585 - 588
Database
ISI
SICI code
1523-7060(20000309)2:5<585:FASOA6>2.0.ZU;2-R
Abstract
[GRAPHICS] The 1,3-oxazine route to enantiopure beta-amido aldehydes was investigated. Heterocycloaddition of the N-acyl imine 1 with (R)-O-vinylpantolactone pro vided the stable dihydroxazine 4c. High diastereocontrols were observed whe n using Yb(fod)(3)-catalyzed or SnCl4-mediated conditions, thus leading aft er quantitative hydrolysis to (R)-N-benzoyl-3-phenylpropanal with >98% ee.