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Advanced organic reactions by Stuart W.

By Stuart W.

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Zn(BH4)2 reduces ketones and aldehydes R4N BH4 organic soluble (CH2Cl2) borohydrides. Synth Commun. 1990, 20, 907 LiEt3BH reduces ketones, aldehydes, esters, epoxides and R-X Li s-Bu3BH reduces ketones, aldehydes, esters and epoxides (hindered borohydride) Na(CN)NH3 reduces iminium ions, ketones and aldehydes Na(AcO)3BH reduces ketones and aldehydes (less reactive) NaBH2S3 reduces ketones and aldehydes REDUCTIONS 41 Sodium Borohydride NaBH4 - reduces aldehydes and ketones to alcohols - does not react with acids, esters, lactones, epoxides or nitriles.

Am. Chem. 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.

Solvent. 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 !

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