Patent ID: 8212049
Filing Date: 2012-07-03
Classification: B01J,C07B,C07F

Abstract:
1. A process of performing an asymmetric hydrogenation, the process comprising reducing a compound of the formula (II) with hydrogen in the presence of a ligand of the formula (I) which is complexed with a transition metal (M) wherein: M is a transition metal for preparing a complex with a ligand of formula (I); Z is independently chosen from hydrogen, aryl ring optionally fused with the phenyl ring, heteroaryl, halogen, alkyl, haloalkyl, alkoxy, cyano, nitro, amino, alkylamino, dialkylamino, —CO X and Y are independently chosen from alkyl and cycloalkyl wherein one of X and Y is an alkyl group, wherein if X and Y are different, the ligands will possess a stereocenter on the phosphorus atom, and this may be of the (R) or (S) absolute configuration, or a mixture of stereoisomers; wherein said X and Y may be a linear or branched alkyl group, which may be unsubstituted or symmetrically substituted with alkyl, aryl, or alkoxy groups, and may contain additional carbon stereocenters, or unsymmetrically substituted with alkyl, aryl, or alkoxy groups, and may contain additional carbon stereocenters; X and Y together with a phosphorus atom may form a ring system, wherein the ring system may be unsubstituted, symmetrically substituted, or unsymmetrically substituted with alkyl, aryl, or alkoxy groups, and may contain additional carbon stereocenters; optionally each X and Y alkyl may be unsaturated and each cycloalkyl may be unsaturated but not aromatic; R1 is chosen from hydrogen, alkyl, branched alkyl, cycloalkyl, aryl chosen from phenyl and naphthyl, heteroaryl, C R2 and R3 can be the same or different and can be chosen from hydrogen, aryl, heteroaryl, alkyl, branched alkyl, cycloalkyl, benzyl, substituted benzyl, each of the above mentioned R2 and R3 are independently optionally substituted with one or more alkyl, halogen, haloalkyl, alkoxy, acyl, phenoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino, carboalkoxy, amido, or sulfoxy group, or R2 and R3 together may form a fused carbocyclic ring; wherein: Ring B represents a 5-membered ring; wherein at least one, or both, of R2 and R3 must be attached to a chiral carbon, of either (R) or (S) absolute configuration, wherein this ring may contain another type of chiral element; and wherein for formula II and III: R R R R and R′ is C1-12 alkyl, benzyl, or naphthylmethyl.