By Stuart W.
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During this quantity, these useful teams containing heteroatoms that experience won significance in natural synthesis are handled intimately. The advent of those numerous teams and their suitable variations are defined and a number of the features of chemoselectivity, regioselectivity and stereoselectivity are mentioned.
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IPr iPr O O Si PhOC(S)Cl, pyridine, DMAP B iPr iPr O nBu3SnH, AIBN PhCH3, reflux B O O > 90% Si O iPr iPr O Si OH iPr iPr O B O O (58-78%) Si O iPr iPr O Si Si O iPr iPr OPh S S OAr O O O CH3 nBu3SnH, AIBN, PhCH3 O O O Tetrahedron 1991, 47, 8969 O 88-91% O O O O Best method for deoxygenation of primary alcohols Ar= 2,4,6-trichlorophenyl, 4-fluorophenyl - N-Phenyl Thionocarbamates iPr iPr O O Si U PhNCS NaH, THF S O Si O iPr iPr Tetrahedron 1994, 34, 10193. iPr iPr O U Si O iPr iPr NHPh (TMS)3SiH, AIBN PhH, reflux S O (78%) O O Si O (93%) iPr iPr O O Si U O Si O iPr iPr NHPh Thiocarbamates - Methyl oxylates OAc O OAc O MeO2CCOCl THF OC nBu3SnH, AIBN PhCH3, reflux OC O HO CO2Me CO2Me MeO2C O OAc O OC CO2Me Methyl Oxylate Esters - Water Soluble Tin Hydride: [MeO(CH2)2O(CH2)3]3SnH / 4,4'-Azo(bis-4-cyanovaleric acid) TL 1990, 31 , 2957 - Silyl Hydride Radical Reducing Agents - replacement for nBu3SnH (Me3Si)3SiH Chem Rev.
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.
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.
Advanced organic reactions by Stuart W.