Asymmetric Synthesis by James D. Morrison (Eds.)

By James D. Morrison (Eds.)

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5) (25). + [Rh(PPh ) R ] 3 2 [Rh(PPh ) H (C=C)] + 2 3 2 [RMPPh^HC-C-C-H)] [Rh(PPh ) ] 3 2 2 — H-C—C—Η (5) However, subsequent studies (3) have revealed that 23 is in equilibrium with a complex ds-[Rh(PPh ) S ] (24) (analogous to [Rh(DIPHOS)S ] , 18), which probably is the active catalyst in the system and that 23 (like the + 3 2 2 + 2 52 J. Halpern analogous complex 22) probably is a dead-end complex (3). Thus, it seems likely that the mechanism depicted by Fig. 1 extends also to rhodium complex catalysts containing monodentate phosphine ligands.

In view of this, it was originally suggested that, in con6 11 3 6 4 3 + + 2 3 2 [Rh(PPh ) (NOR)] 3 + 2 - norbornane (4) Ph,P/ Ph,P -H2 Rh Rh Ρη,Ρ' PPh, s 24 23 trast to the "olefin route" of olefin hydrogenation depicted in Fig. 1 for [Rh(DIPHOS)] , hydrogenation with catalysts containing monodentate phosphine ligands proceeds by the alternative "hydride route" depicted by Eq. (5) (25). + [Rh(PPh ) R ] 3 2 [Rh(PPh ) H (C=C)] + 2 3 2 [RMPPh^HC-C-C-H)] [Rh(PPh ) ] 3 2 2 — H-C—C—Η (5) However, subsequent studies (3) have revealed that 23 is in equilibrium with a complex ds-[Rh(PPh ) S ] (24) (analogous to [Rh(DIPHOS)S ] , 18), which probably is the active catalyst in the system and that 23 (like the + 3 2 2 + 2 52 J.

It is, of course, necessary to select compounds where the structural features allow the diphosphinite to form chelate rings. The phosphinite function needs to be handled with some care because it is sensitive to oxidation, hydrolysis, and Η. Β. Kagan 24 alcoholysis. Some diphosphinites are thermally unstable and difficult to handle (75). Diphosphinites were mainly used as ligands for rhodium asymmetric hydrogenation catalysts. The most useful ligands are listed in above, with references. For example, ligands 90 and 91 gave 80 and 90% ee, respectively, in asymmetric reductions of N-acetyl-a-amino-cinnamic acid (76, 77).

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