Catalytic Enantioselective Synthesis of Glutamic Acid Derivatives via Tandem Conjugate Addition−Elimination of Activated Allylic Acetates under Chiral PTC Conditions

• Published in: Journal of the American Chemical Society Vol. 127; no. 39; pp. 13450 - 13451
• Main Authors: Ramachandran, P. Veeraraghavan, Madhi, Sateesh, Bland-Berry, Layla, Ram Reddy, M. Venkat, O'Donnell, Martin J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.10.2005; Amer Chemical Soc
• Subjects: Acetates - chemistry; Aliphatic compounds; Catalysis; Chemistry; Chemistry, Multidisciplinary; Crystallography, X-Ray; Exact sciences and technology; Glutamic Acid - chemical synthesis; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; VINYLALUMINATION; ALKYLATION; QUATERNARY AMMONIUM-SALTS; ESTERS; PHASE-TRANSFER CATALYSIS; ALPHA-AMINO-ACIDS; RECEPTORS; Phase transfer catalysis; Organic synthesis; α-Aminoacid; Catalytic reaction; Enantioselectivity; Asymmetric synthesis; Addition reaction; Dicarboxylic acid; Tandem reaction
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja052638m

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).