By Rizzo C.J.

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J. Chem. 1970, 48 , 735. Lalancette Reduction 42 NaBH4/ NiCl 2 Chem. Pharm. Bull. 1981, 29 , 1159; Chem. Ber. 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.

R R S R Raney Nickel R H R H (CH 2)n O R S 31 REDUCTIONS O O O O O HO 32 O HO Raney Nickel JOC 1987, 52, 3346 EtOH (74%) H S H S Homogeneous Catalytic Hydrogenation - catalyst is soluble in the reaction medium - catalyst not "poisoned" by sulfur - very sensitive to steric effects - terminal olefins faster than internal; cis olefins faster than trans R R > > R R R R > R R R > R R >> R R R - (Ph3P)3RhCl (Wilkinson's Catalyst); [R3P Ir(COD)py]+ PF6- (Crabtree's Catalyst) (Ph3P)3RhCl, H2 OH OH JOC 1992, 57, 2767 C 6H6 (92%) Directed Hydrogenation Review: Angew.

100%) O O H O H O BINAL-H (Noyori) - Chiral aluminium hydride for the asymmetric reduction of prochiral ketones OH OH 1) LiAlH4 2) ROH H O Li + Al O OR R= Me, Et, CF 3CH 2- BINOL BINAL-H O O O BINAL-H,THF Tetrahedron 1990, 46 , 4809 -100 to -78°C HO (94% ee) Intermediate for 3-Component Coupling Strategy to Prostaglandins I O Li+ O CO 2Me RO Li+ RCu RO OTBS O OTBS O CO 2H CO 2Me HO RO OTBS OH PGE 2 REDUCTIONS Alane 50 AlH3 LiAlH 4 + AlCl3 → AlH3 - superior to LAH for the 1,2-reduction of α,β-unsaturated carbonyls to allylic alcohols OMe Ph 1) AlH3, ether, 0°C 2) H3O + O O HO O Me O JACS 1989, 111 , 6649 Me O OH O Diisobutyl Aluminium Hydride DIBAL or DIBAL-H Al H - Reduces ketones and aldehydes to alcohols - reduces lactones to hemi-acetals O Al O OH CHO work up DIBAL O (CH 2)n O OH O (CH 2)n (CH 2)n (CH 2)n lactol (stable complex) - reduces esters to alcohols - under carefully controlled reactions conditions, will partially reduce an ester to an aldehyde Al O DIBAL R CO 2Me if complex is unstable R C OMe fast R CHO R CH 2 OH H if complex is stable R CHO O O O OBn O DIBAL, CH 2Cl 2 O HO OH HO HO H O HO OBn O OBn OH OBn OH JACS 1990, 112 , 9648 OBn OBn DIBAL, CH 2Cl 2 CO 2iPr iPrO2C OHC OBn O R OBn O TMS-Cl, Et3N OH CHO CH2Cl2 R O DiBAl-H OSiMe3 CH2Cl2, -78°C TL 1998, 39, 909 R H Reduction of O-Methyl hydroxamic acids O R O R'-M R' R O OMe N Me TL 1981, 22 , 3815 DIBAL or LAH R H REDUCTIONS 51 Sodium Bis(2-Methoxyethoxy)Aluminium Hydride REDAL Organic Reactions 1988, 36, 249 Organic Reactions 1985, 36, 1.

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