title: Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles.
abstract: A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Netz
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Murat
authors.initials: M
authors.lastname: Kucukdisli
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
chemical_list: C000604972:5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane; D000596:Amino Acids; D004146:Dioxanes; D009570:Nitriles; D011522:Protons