TY - JOUR
T1 - Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition - Elimination of activated allylic acetates under chiral PTC conditions
AU - Ramachandran, P. Veeraraghavan
AU - Madhi, Sateesh
AU - Bland-Berry, Layla
AU - Reddy, M. Venkat Ram
AU - O'Donnell, Martin J.
PY - 2005/10/5
Y1 - 2005/10/5
N2 - 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).
AB - 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).
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U2 - 10.1021/ja052638m
DO - 10.1021/ja052638m
M3 - Article
C2 - 16190680
AN - SCOPUS:26044441701
SN - 0002-7863
VL - 127
SP - 13450
EP - 13451
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 39
ER -