title: Catalytic asymmetric syntheses of alpha-amino and alpha-hydroxyl acid derivatives.
abstract: Herein we report the first room temperature Heck reaction of aryl bromides and CH(2)=C(NHP)CO(2)Me (P = Boc or CBz) to form ArCH=C(NHP)CO(2)Me, which are then used for the asymmetric syntheses of alpha-amino acids. We also report the first syntheses of ArCH=C(OCOAr(1))CO(2)Me (Ar(1) = Ph, 4-Cl-Ph) from ArBr and CH(2)=C(OCOAr(1))CO(2)Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford alpha-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.
authors.affiliation: Neuroscience Discovery Chemistry, Research & Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA. xiaojun.han@bms.com
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Han
authors.forename: Xiang-Jun
authors.initials: XJ
authors.lastname: Jiang
authors.forename: Rita L
authors.initials: RL
authors.lastname: Civiello
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Degnan
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Chaturvedula
authors.forename: John E
authors.initials: JE
authors.lastname: Macor
authors.forename: Gene M
authors.initials: GM
authors.lastname: Dubowchik
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
chemical_list: D000596:Amino Acids; D001965:Bromides; D004952:Esters; D006878:Hydroxides; C031356:hydroxide ion