Han Xiaojun, Jiang Xiang-Jun, Civiello Rita L, Degnan Andrew P, Chaturvedula Prasad V, Macor John E, Dubowchik Gene M
Neuroscience Discovery Chemistry, Research & Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
J Org Chem. 2009 May 15;74(10):3993-6. doi: 10.1021/jo900368k.
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.