title: Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition-elimination of activated allylic acetates under chiral PTC conditions.
abstract: A new, general, and practical procedure for the asymmetric synthesis of 4-alkylidenyl glutamic acid derivatives via a catalytic enantioselective tandem conjugate addition-elimination on allylic acetates under chiral phase-transfer conditions is reported. A variety of structural types of allylic acetates have been reacted with the benzophenone imine of glycine tert-butyl ester to give the products in good to excellent yields and enantioselectivities (63-92% yield, 80-97% ee, 8 cases).
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
authors.forename: P Veeraraghavan
authors.initials: PV
authors.lastname: Ramachandran
authors.forename: Sateesh
authors.initials: S
authors.lastname: Madhi
authors.forename: Layla
authors.initials: L
authors.lastname: Bland-Berry
authors.forename: M Venkat
authors.initials: MV
authors.lastname: Ram Reddy
authors.forename: Martin J
authors.initials: MJ
authors.lastname: O'Donnell
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D018698:Glutamic Acid / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D018698:Glutamic Acid