A new method for the synthesis of chiral beta-branched alpha-amino acids.
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.
Spangenberg
Thomas
T
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.
Schoenfelder
Angèle
A
Breit
Bernhard
B
Mann
André
A
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