title: Cumyl ester as the C-terminal protecting group in the enantioselective alkylation of glycine benzophenone imine.
abstract: Cumyl ester is an optimal C-terminal protecting group for glycine benzophenone imine in asymmetric alkylation reactions catalyzed by Cinchona chiral phase-transfer catalysts. High levels of enantioselectivity have been obtained (up to 94% ee) with this substrate, which provides an attractive alternative to the analogous tert-butyl ester. N-terminal imines and the C-terminal esters can be cleaved from alkylation products by hydrogenolysis, while maintaining acid-labile side chain protecting groups.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Respondek
authors.forename: Eric
authors.initials: E
authors.lastname: Cueny
authors.forename: Jeremy J
authors.initials: JJ
authors.lastname: Kodanko
mesh_terms: D000478:Alkylation; D001577:Benzophenones / Q000737:chemistry*; D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001577:Benzophenones; D004952:Esters; D007097:Imines; D005998:Glycine