D. A. Evans Diastereoaselective Hydrogenation: Cyclic Substrates Chem 206 Polar functional groups other than OH may also direct the process COmE COmE Ir(pyr)Pcy3 Diastereoselection Rh(DIPHOS-4)+ tereoselection 55:45 99 CO2 Me X Diastereoselection diastereoselection Ir(pyr)Pcy3 OMe 99:1 89:11 CH .G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, diastereoselection OCH3 15 psi H2 OCH J.M. Brown and S.A. Hall, J. Organomet chem., 1985, 285, 333 ereoselecton Ir(pyr)Pcy3 diastereoselection RH >99:1 H Crabtree and M.W. Davis, J. Org. Chem., 1986, 51, 2655 H CHrOMe 15 psi H2 Ir(pyr)Pcy3'CH3Lo diastereoselection 99 diastereoselection >99:1 A.G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, 50, 5907 A.G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, 50, 590O N Me CO2Me CH3 CO2Me H2C CO2Me CH3 CO2Me CH3 Me O N H CH3 O X CH3 Me O X OCH3 CH3 N N Me H H O H O H N H O H O H H Me N CH2OMe N CH3 O CH3 CH3 O N CH3 CH2OMe CH3 CONC4H8 CH3 X O CH3 X O Me CH3 OCH3 CONC4H8 CH3 X X OMe NC4H8 OMe NC4H8 D. A. Evans Diastereoaselective Hydrogenation: Cyclic Substrates Chem 206 Polar functional groups other than OH may also direct the process A.G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, 50, 5907. J.M. Brown and S.A. Hall, J. Organomet. Chem., 1985, 285, 333. Ir(pyr)Pcy3 + H2 diastereoselection 91 : 9 H2 Ir(pyr)Pcy3 + Rh(DIPHOS-4)+ H2 diastereoselection 89:11 diastereoselection >99:1 Ir(pyr)Pcy3 + H2 diastereoselection >99:1 H2 Ir(pyr)Pcy3 + Diastereoselection 55:45 99:1 Ir(pyr)Pcy3 + H2 99:1 >99:1 Diastereoselection H2 Ir(pyr)Pcy3 + diastereoselection >99:1 A.G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, 50, 5907. 15 psi H2 Ir(pyr)Pcy3 + R.H. Crabtree and M.W. Davis, J. Org. Chem., 1986, 51, 2655. 15 psi H2 Ir(pyr)Pcy3 + diastereoselection >99:1 diastereoselection >99:1 A.G. Schultz and P.J. McCloskey, J. Org. Chem., 1985, 50, 5907