Institute of Medicinal Chemistry, University of Urbino Carlo Bo, Piazza Rinascimento 6, 61029 Urbino (PU), Italy.
Chem Asian J. 2010 Mar 1;5(3):550-4. doi: 10.1002/asia.200900441.
A clean, efficient, and diasteroselective (dr >95%) catalytic hydrogenation of the enamide N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide (2 a) using palladium on carbon is performed. This procedure provides the melatonin receptor ligand (+/-)-cis-4-phenyl-2-propionamidotetralin (cis-4-P-PDOT, 1 a) and its 8-methoxy analog. Furthermore, Rh and Ru catalyzed homogeneous asymmetric hydrogenation of the challenging racemic endocyclic enamide 2 a with several chiral phosphine ligands is studied. The best results, in terms of enantioselectivity, for both diastereomers are obtained when chiral Rh-Josiphos is used as the catalyst.
使用钯碳对烯酰胺 N-(4-苯基-3,4-二氢萘-2-基)丙酰胺（2 a）进行了清洁、高效和非对映选择性（dr >95%）的催化氢化。该方法提供了褪黑素受体配体（±）-顺式-4-苯基-2-丙酰胺四氢萘（cis-4-P-PDOT，1 a）及其 8-甲氧基类似物。此外，还研究了 Rh 和 Ru 催化的具有几种手性膦配体的挑战性内环烯酰胺 2 a 的均相不对称氢化。使用手性 Rh-Josiphos 作为催化剂时，两种非对映异构体的对映选择性均获得最佳结果。
