Patent ID: 7528267
Filing Date: 2009-05-05
Classification: C07D

Abstract:
1. A method for preparing enantioselectively an enantiomeric chromane (compound (I)): wherein each R 4 , R 5 , R 6 , and R 7 is independently selected from the group consisting of H, OH, phenyl, aryl, alkyl, alkylaryl, arylalkyl, OR 8 , OC(O)R 8 , OS(O)R 8 , thio, alkylthio, mercaptal, alkylmercaptal, amino, alkylamino, dialkylamino, nitro and halo, and where R 8 is alkyl and alkylaryl; and R 1 , R 2 , and R 3 is independently selected from —R 4 and wherein each R 9 , R 10 , R 11 , R 12 , and R 13 is independently selected from H and R 4 ; comprising the steps of: 1) providing a chromene compound selected from: 2) hydrogenating the chromene in the presence of an Ir catalyst having a chiral ligand shown as compound (V): to form the corresponding chromane; wherein each of Y and X is independently selected form the group consisting of S, O and N, and each R 14 and R 15 is independently selected from the group consisting of alkyl, aryl, phenyl, alkylaryl, and arylalkyl.