Diastereoselective cycloadditions of chiral non-racemic azomethine imines

Citation
F. Roussi et al., Diastereoselective cycloadditions of chiral non-racemic azomethine imines, SYNTHESIS-S, (8), 2000, pp. 1170-1179
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
8
Year of publication
2000
Pages
1170 - 1179
Database
ISI
SICI code
0039-7881(200007):8<1170:DCOCNA>2.0.ZU;2-1
Abstract
(SR)-5-Phenyl[1,3,4]oxadiazinan-2-one (6) is an easily available building b lock and acts as a chiral non-racemic precursor for azomethine imines. The ylid can be formed regioselectively with various aldehydes and reacts in an efficient manner with a wide range of dipolarophiles. The regio- and diast ereoselectivity of the cycloadditions have been fully investigated and can lead, in the best cases, to the creation of three contiguous asymmetric cen ters in a single step, with complete control of relative and absolute confi gurations.