Catalytic asymmetric syntheses of alpha-amino and alpha-hydroxyl acid derivatives.
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.
Han
Xiaojun
X
Neuroscience Discovery Chemistry, Research & Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA. xiaojun.han@bms.com
Jiang
Xiang-Jun
XJ
Civiello
Rita L
RL
Degnan
Andrew P
AP
Chaturvedula
Prasad V
PV
Macor
John E
JE
Dubowchik
Gene M
GM
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
D000596:Amino Acids; D001965:Bromides; D004952:Esters; D006878:Hydroxides; C031356:hydroxide ion