On the mechanism of an asymmetric α, β-unsaturated carboxylic acid hydrogenation: application to the synthesis of a PGD2 receptor antagonist

…, JC McWilliams, G Humphrey, M Journet…

Index: Tellers, David M.; McWilliams, J. Christopher; Humphrey, Guy; Journet, Michel; DiMichele, Lisa; Hinksmon, Joseph; McKeown, Arlene E.; Rosner, Thorsten; Sun, Yongkui; Tillyer, Richard D. Journal of the American Chemical Society, 2006 , vol. 128, # 51 p. 17063 - 17073

Full Text: HTML

Citation Number: 26

Abstract

Ruthenium complexes employing axially chiral ligands were found to be effective asymmetric hydrogenation catalysts for the reduction of α, β-unsaturated ene acid 1-E to give 2, a prostaglandin D2 (PGD2) receptor antagonist. With [(S-BINAP) Ru (p-cymene) Cl2] 2 (3, S-BINAP=(S)-(+)-2, 2'-bis (diphenylphospino)-1, 1'-binapthyl), it was discovered that low hydrogen pressures (< 30 psi) were essential to achieve high enantioselectivities (92 ...