ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS

Authors
KOCH SSC CHAMBERLIN AR
Citation
Ssc. Koch et Ar. Chamberlin, ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS, Journal of organic chemistry, 58(10), 1993, pp. 2725-2737
Citations number
224
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
10
Year of publication
1993
Pages
2725 - 2737
Database
ISI
SICI code
0022-3263(1993)58:10<2725:EPOBFF>2.0.ZU;2-J
Abstract
An efficient and general enantioselective synthesis of beta-alkyl-gamm a-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacet al that proceeds with excellent regiochemical control and high diaster eofacial selectivity. Reductive removal of the chiral auxiliary follow ed by acid-induced cyclization of the resultant hydroxy ketene dithioa cetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.