Catalytic Enantioselective Synthesis of Glutamic Acid Derivatives via Tandem Conjugate Addition−Elimination of Activated Allylic Acetates under Chiral PTC Conditions
Journal of the American Chemical Society2005Vol. 127(39), pp. 13450–13451
Citations Over TimeTop 10% of 2005 papers
P. Veeraraghavan Ramachandran, Sateesh Madhi, Layla Bland‐Berry, M. Venkat Ram Reddy, Martin O’Donnell
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).
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