Advanced Organic Reactions by Rizzo C.J.

By Rizzo C.J.

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Soc. 1987, 109, 1596 O Vitamin E REDUCTIONS 39 Kinetic Resolution by Directed Hydrogenation CF 3SO 3- Rh+ MeO Ph P P Ph CO 2Me MeO 2C H2 (15 psi), L*Rh+ Et Ph OMe CO 2Me MeO 2C 0 °C (~60% conversion) R R= OMe R > 96 % ee 82 % 93 % Hydrogenation of Carbonyls 1,3-diketones: O R1 O O R1 OH H2 O H OH OH R2 R2 R1 O H O H syn anti Ru2Cl 4(BINAP) Et3N, H2 (100 atm) MeO 2C 99 : 1 16 : 1 (90 % ee) 32 : 1 49 : 1 R1 R2 R1 R2 Directed Reduction M O R1 anti : syn= OH R1 O R2 OH syn anti H O M OH R2 -CH3 -CH2CH3 -iPr -CH2CH3 R2 R2 + R1 R2= OH R1 OH R2 -CH3 -CH3 -CH2CH3 -CH2CH3 O R2 Ru (II) H2 (700 psi) O R1 O R1 R2 O R1= OH O OH JACS 1988, 110 , 6210 MeO 2C (98% ee) Decarbonylations O (Ph3P)3RhCl O (Ph3P)3RhCl R H R H - CO R Cl R Cl - CO REDUCTIONS 40 OHC (Ph3P)3RhCl Fe Fe Fe PhCH 3, ∆ JOC 1990, 55, 3688 Fe Diimide HN=NH Review: Organic Reactions 1991, 40J.

Rev. 1986, 86, 763 Org. Rxn. 1951, 6, 469. Lithium Aluminium Hydride LiAlH4 (LAH) - very powerful reducing agent - used as a suspension in ether or THF - Reduces carbonyl, carboxylic acids and esters to alcohols - Reduces nitrile, amides and aryl nitro groups to amines - opens epoxides - reduces C-X bonds to C-H - reduces acetylenic alcohols trans-allylic alcohols LAH OH R OH R H2N LAH, THF N H NH 2 H2N (62%) NH 2 N H NH 2 Lindlar/ H2 H2N O N H HO CO 2Me OH LAH, THF, ↑↓ TL 1988, 29 , 2793. (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.

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. acetylenes + H2, Pd/BaSO4/ quinoline → cis olefins Acid Chlorides + H2, Pd/BaSO4 → Aldehydes R SiMe 3 (Lindlar Reduction) (Rosemund Reduction) Org. Rxn. O. House Modern Synthetic Reactions, 2nd edition) R COCl R CHO R NO 2 R NH 2 R R' R R CH 2-OH R CHO R CH CH R CH 2 CH 2 R' R' O R HO H R' Ar R' R O R R' Ar CH 3 + HO R R CH 2 NH 2 R C N O R CH 2-OH R + HO R' OR' O R' R R N CH 2 R' N R' R' requires high temperature & pressure R CO 2- Na+ no reaction Raney Nickel Desulfuriztion , Reviews: Org.

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