Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition - Elimination of activated allylic acetates under chiral PTC conditions

P. Veeraraghavan Ramachandran, Sateesh Madhi, Layla Bland-Berry, M. Venkat Ram Reddy, Martin J. O'Donnell

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

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).

Original languageEnglish (US)
Pages (from-to)13450-13451
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number39
DOIs
StatePublished - Oct 5 2005

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