AN ASYMMETRIC NITROOLEFINATION OF ALPHA-ALKYL-GAMMA-LACTONES AND DELTA-LACTONES WITH MODIFIED NITROENAMINES

Authors
NISHIDE K KUROSAKI R HOSOMI K IMAZATO H INOUE T NODE M OHMORI T FUJI K
Citation
K. Nishide et al., AN ASYMMETRIC NITROOLEFINATION OF ALPHA-ALKYL-GAMMA-LACTONES AND DELTA-LACTONES WITH MODIFIED NITROENAMINES, Tetrahedron, 51(40), 1995, pp. 10857-10866
Citations number
52
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
40
Year of publication
1995
Pages
10857 - 10866
Database
ISI
SICI code
0040-4020(1995)51:40<10857:AANOAA>2.0.ZU;2-#
Abstract
New chiral nitroenamines 4a,b having (S)-2-t-butyldimethylsiloxymethyl pyrrolidine as an auxiliary were found to be very effective for asymme tric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The en antiomeric excess of the product increased remarkably in the reaction with gamma-lactones compared with previous nitroenamines 1a,b. A possi ble chelation model for the transition state of the asymmetric nitrool efination is discussed.