ASYMMETRIC LEWIS ACID-CATALYZED ADDITION OF A KETENE DITHIOACETAL TO A CHIRAL BICYCLIC LACTAM - FORMATION OF CYCLOBUTANOPYRROLIDINONES - A NEW CLASS OF GABA DERIVATIVES

Authors
MEYERS AI TSCHANTZ MA BRENGEL GP
Citation
Ai. Meyers et al., ASYMMETRIC LEWIS ACID-CATALYZED ADDITION OF A KETENE DITHIOACETAL TO A CHIRAL BICYCLIC LACTAM - FORMATION OF CYCLOBUTANOPYRROLIDINONES - A NEW CLASS OF GABA DERIVATIVES, Journal of organic chemistry, 60(14), 1995, pp. 4359-4362
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
14
Year of publication
1995
Pages
4359 - 4362
Database
ISI
SICI code
0022-3263(1995)60:14<4359:ALAAOA>2.0.ZU;2-U
Abstract
Additions to unsaturated chiral lactams 8 using methylenedithiolane, g ave very high endo-selectivity of the cyclobutane adducts (2 + 2 addit ion) 13, 16. Removal of the phenylglycinol auxiliary by reductive clea vage produced the title compound (+)-20 in very high (>99%) enantiomer ic excess. Absolute stereochemistry of the cyclobutanopyrrolidinone, c ontaining three contiguous stereocenters, was confirmed by X-ray cryst allography.