Advanced organic reactions by Stuart W.

By Stuart W.

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Acid Chlorides O O O O N N + N R R OH R R N Cl + N N acyl pyridinium ion (more reactive) 1. SOCl2 2. PCl5 3. (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.

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. OH O CO 2Me CO 2Me NaBH 4/ CeCl3 EtOH, H2O CHO CHO O CeCl 3 H2O 1) NaBH 4, CeCl3 2) work-up R JACS 1979, 101 , 5848 OH OH O OH CHO NaBH 4/ CeCl3 EtOH, H2O (78%) CHO REDUCTIONS Zinc Borohydride Zn(BH4)2 Synlett 1993, 885.

Chem. 1975, 94 , 449 O O O iPr3SiH, Et2O Si O 2 Pt 2 OSi(iPr)3 O JOC 1994, 59, 2287 O (87%) - Buchwald Reduction JACS 1991, 113 , 5093 - catalytic reagent prepared from Cp2TiCl2 + nBuLi and stoichometric (Et)3SiH in THF will reduce ester, ketones and aldehydes to alcohols under very mild conditions. - α,b− unsaturated esters are reduced to allylic alcohols - free hydroxyl groups, aliphatic halides and epoxides are not reduced REDUCTIONS 54 Clemmensen Reduction Organic Reactions 1975, 22, 401 Comprehensive Organic Synthesis 1991, vol 8, 307.

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