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5 mol % Catalyst 50 : 1 150 : 1 33 : 1 52 : 1 OH REDUCTIONS 34 Olefin Isomerization: CH3 (3 : 1) OH OH olefin isomerization O OH major product - Conducting the hydrogenation at high H 2 pressures supresses olefin isomerization and often gives higher diastereoselectivity. Other Lewis basic groups can direct the hydrogenation. (Ir seems to be superior to Rh for these cases) OMe CO2Me OMe Ir CO2Me + Ir+ 99 : 1 O O CO2H Ir+ 7 : 1 Rh+ 1 : 1 O O N O O N O 130 : 1 1:1 Acyclic Examples Rh+ (2 mol %) OH Me CH 3 JCSCC 1982, 348 H2 (15 psi) Me L L M OH (97:3) H O OH H H Ph H 3C H H L CH3 Ph M L Ph anti H H O H 32 : 1 CO2H > 99 : 1 O > 99 : 1 Rh+ OH 1,2-strain Ph syn REDUCTIONS L L R3 H OH R3 35 H O M R2 R1 OH favored R3 H syn R1 R2 R1 R2 R3 H L H R1 R2 M OH disfavored R3 1,2-strain R1 R2 O H L anti - Supression of olefin isomerization is critical for acyclic stereocontrol !

COCl)2 Anhydrides O O P2O 5 2 R OH R O O R Activating Agents: Carbonyl Diimidazole O O O R OH N + N R N N N N Acyl Imidazole NH + CO + N PROTECTING GROUPS 63 Dicyclohexylcarbodiimide C 6H11 O NH O R + OH R N C N O O Nu: O C N R +C 6H11 Nu N H N H C 6H11 C 6H11 Ketene formation is a common side reaction- scambling of chiral centers C 6H11 O NH R R O C N H C O "ketene" C 6H11 Hydroxybenzotriazole (HOBT) - reduces ketene formation C 6H11 O R O N NH + O C N N N O N R N N OH C 6H11 N-Hydroxysuccinimide (NHS) O C 6H11 O R O O NH HO + O C N R N O N O C 6H11 O 2,2'-Dipyridyl Disulfide (Aldrithiol, Corey Reagent) Aldrichimica Acta 1971, 4 , 33 O R OH O Ph3P: + N S S R N + S + N N Ph3P=O SH Mukaiyama's Reagent (2-Chloro-1-methyl pyridinium Iodide or 2-Fluoro-1methyl pyridinium p-toulenesulfonate) Aldrichimica Acta 1987, 20 , 54 Chem.

1984, 117 , 856. Ar-NO2 → Ar-NH2 Ar-NO → Ar- NH2 R2C=N-OH → R2CH-NH2 NaBH4 / TiCl 4 Synthesis 1980, 695. R-COOH → R-CH2-OH R-COOR' → R-CH2-OH R-CN → R-CH2-NH2 R-CONH2 → R-CH2-NH2 R2C=N-OH → R2CH-NH2 R-SO2-R' → R-S-R' NaBH4 / CeCl 3 Luche Reduction reduced α,β-unsaturated ketones in a 1,2-fashion OH NaBH 4/ CeCl3 R R NaBH 4 R R O OH O R + R R R R R R H R JCSCC 1978, 601 JACS 1978, 100 , 2226 O OH CO 2Me NaBH 4/ CeCl3 C 5H11 CO 2Me MeOH C 5H11 OH OH - selective reduction of ketones in the presence of aldehydes.

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