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.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
**Corresponding author.
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