PRACTICAL ASYMMETRIC APPROACH TO PYRROLIDINONES - EFFICIENT SYNTHESISOF (-PREUSSIN AND (-)-AHPPA())

Authors
KANAZAWA A GILLET S DELAIR P GREENE AE
Citation
A. Kanazawa et al., PRACTICAL ASYMMETRIC APPROACH TO PYRROLIDINONES - EFFICIENT SYNTHESISOF (-PREUSSIN AND (-)-AHPPA()), Journal of organic chemistry, 63(14), 1998, pp. 4660-4663
Citations number
57
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
14
Year of publication
1998
Pages
4660 - 4663
Database
ISI
SICI code
0022-3263(1998)63:14<4660:PAATP->2.0.ZU;2-E
Abstract
A novel, dichloroketene-chiral enol ether cycloaddition-based synthesi s of enantiopure (+)-preussin and (-)-AHPPA has been realized. The eff icient, highly stereoselective approach, which involves a Beckmann rin g expansion reaction to access the key pyrrolidinone, proceeds in ca. 16% overall yield for each of the compounds.