title: Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.
abstract: The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Cedric L
authors.initials: CL
authors.lastname: Hugelshofer
authors.forename: Kevin T
authors.initials: KT
authors.lastname: Mellem
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Myers
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000661:Amphetamine / Q000737:chemistry*; D004952:Esters; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000596:Amino Acids; D004952:Esters; D007783:Lactones; C042908:validamine; D007294:Inositol; D000661:Amphetamine; D000409:Alanine