title: A new method for the synthesis of chiral beta-branched alpha-amino acids.
abstract: A new method for the synthesis of chiral beta-branched alpha-amino acids based on a copper-mediated directed allylic substitution reaction with Grignard reagents is reported. This is the first case in which a delta-stereogenic center is controlling the diastereoselectivity of an o-DPPB-directed allylic substitution. Depending on the alkene geometry of the starting material either diastereomer, anti or syn, is accessible with good levels of acyclic stereocontrol.
authors.affiliation: Département de Pharmacochimie de la Communication Cellulaire UMR 7175-LC-1 ULP/CNRS, Faculté de Pharmacie 74 route du Rhin BP 60024, F-67401 Illkirch, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Spangenberg
authors.forename: Angèle
authors.initials: A
authors.lastname: Schoenfelder
authors.forename: Bernhard
authors.initials: B
authors.lastname: Breit
authors.forename: André
authors.initials: A
authors.lastname: Mann
mesh_terms: D000545:Amanita / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D020148:Butyric Acid / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism