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Rxns. 1989, 37, 1. OAc Porcine Pancreatic Lipase TL 1988, 30 , 6189 OAc OH (96% ee) Chloroacetates - can be selectively cleaved with Zn dust or thiourea. O Me O OR O HO AcO Me OAc O Cl Me O OR Cl H2NNHCOSH O AcO Me O JCS CC 1987, 1026 O OAc O HO Cl O O OH O Trifluoroacetates Formation: - with trifluoroacetic anhydride or trifluoroacetyl chloride Cleavage: - K2CO3, MeOH Pivaloate (t-butyl ester) - Fairly selective for primary alcohols Formation: - tbutylacetyl chloride or t-butylacetic anhydride Cleavage: - removed with mild base Benzoate (Bz) - more stable to hydrolysis than acetates.

Boron Reagents 3. Aluminium Reagents 4. Tin Hydrides 5. Silanes 6. Dissolving Metal Reductions Hydrogenations Heterogeneous Catalytic Hydrogenation Transition metals absorbed onto a solid support metal: Pd, Pt, Ni, Rh support: Carbon, alumina, silica solvent: EtOH, EtOAc, Et2O, hexanes, etc. - Reduction of olefins & acetylenes to saturated hydrocarbons. e. hydroxyls, can sometimes direct the delivery of H2. Cis addition of H2. R1 R1 R2 R2 H H2, Pd/C R1 H R2 R1 R2 - Catalyst can be "poisoned" - Directed heterogeneous hydrogenation O O H H2, Pd/C O O OH MeO O OH MeO H2, Pd/C H O O CO2Me MeO O CO2M2 (86 : 14) MeO Lindlar Catalyst ( Pd/ BaSO4/ quinoline)- partially poisoned to reduce activity; will only reduce the most reactive functional groups.

1985, 26, 6005 Rh+ (20 mol %) OH OH H2 (15 psi) OBz OBz TBSO 8:1 TBSO Asymmetric Homogeneous Hydrogenation - Chiral ligands for homogeneous hydrogenation of olefins and ketones H O P OMe MeO PPh2 PPh2 O P H DIOP PPh2 PPh2 PPh2 PPh2 PPh2 PPh2 R= -CH3 PROPHOS = -Ph PHENPHOS = -C6H11 CYCPHOS CHIRAPHOS DBPP DIPAMP Ph2P PPh2 PPh2 X PPh2 CO2tBu BPPM PPh2 CO 2H Ph HN PPPFA PPh2 P BINAP DIPHEMP Rh (I) L*, H2 CO 2H Ph HN Ph (95% ee) O CO 2Me Ph O CO 2H NHAc O NH 2 HO O OH L-DOPA DIOP DIPAMP PPPFA BINAP NORPHOS BPPM 85% ee 96% ee 93% ee 100% ee 95% ee 91% ee PPh2 PPh2 PPh2 PPh2 DUPHOS Fe N X= CH2 DPCP X= N-R PYRPHOS CAMPHOS P PPh2 PPh2 PPh2 PPh2 NORPHOS NMe2 ACR 1983, 16, 106.

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Advanced organic reactions by Stuart W.


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