title: Syn-Selective Synthesis of β-Branched α-Amino Acids by Alkylation of Glycine-Derived Imines with Secondary Sulfonates.
abstract: A syn-selective synthesis of β-branched α-amino acids has been developed based on the alkylation of glycine imine esters with secondary sulfonates. The potassium counterion for the enolate, the solvent, and the leaving group on the electrophile were key levers to maximize the diasteroselectivity of the alkylation. The optimized conditions enabled a straightforward preparation of a number of β-branched α-amino acids that can be challenging to obtain.
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Sha
authors.initials: S
authors.lastname: Lou
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Grace M
authors.initials: GM
authors.lastname: McKenna
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Steven A
authors.initials: SA
authors.lastname: Tymonko
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Antonio
authors.initials: A
authors.lastname: Ramirez
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Tamas
authors.initials: T
authors.lastname: Benkovics
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: David A
authors.initials: DA
authors.lastname: Conlon
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive , New Brunswick, New Jersey 08903, United States.
authors.forename: Francisco
authors.initials: F
authors.lastname: González-Bobes
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids; D002384:Catalysis; D004952:Esters; D005998:Glycine / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D007097:Imines; D013451:Sulfonic Acids; D005998:Glycine