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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 77-83

http://dx.doi.org/10.1351/pac200274010077

Recent studies on asymmetric hydrogenation. New catalysts and synthetic applications in organic synthesis

Jean Pierre Genet

École Nationale Supérieure de Chimie de Paris, Laboratoire de Synthèse Sélective Organique et Produits Naturels, 11 rue Pierre & Marie Curie, 75231 Paris Cedex 05, France

Abstract: CODRu(h3methylallyl)2 is a versatile starting material for the preparation of a wide range of chiral bisphosphines ruthenium(II) complexes: (P*P)Ru(h3methylallyl)2 2, Ru[X4(P*P)2] 3, and cationic monohydride ruthenium complex 4. A facile synthesis of new C2 electron-rich chiral phosphines, bis(phosphetano)benzene 8 and 1,1¢bis(phosphetano)ferrocene 10 is presented. Dynamic kinetic resolution was used for efficient syntheses of key components of the hexahydroazepane core 16 of balanol and of optically pure Boc-(2S,3R,3S)-iso-dolaproïne 19. Catalyst 4 was used in asymmetric hydrogenation of 22 to give (+)-cis-methyl dihydrojasmonate in high enantioselectivity.