Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition-elimination of activated allylic acetates under chiral PTC conditions.
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).
Ramachandran
P Veeraraghavan
PV
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
Madhi
Sateesh
S
Bland-Berry
Layla
L
Ram Reddy
M Venkat
MV
O'Donnell
Martin J
MJ
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D018698:Glutamic Acid / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000085:Acetates; D018698:Glutamic Acid