Selectivity - SELECTIVITY SELECTIVITY Science 1983, 219,...

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SELECTIVITY 1 SELECTIVITY Science 1983 , 219 , 245 Chemoselectivity preferential reactivity of one functional group (FG) over another - Chemoselective reduction of C=C over C=O: O H 2 , Pd/C O - Chemoselective reduction of C=O over C=C: O NaBH 4 OH O + O NaBH 4 , CeCl 3 OH only - Epoxidation: OH OH OH + MCPBA O O (2 : 1) OH OH O VO(acac) 2 , tBuOOH exclusively Regioselectivity - Hydration of C=C: R R OH R OH 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 1) B 2 H 6 2) H 2 O 2 , NaOH - Friedel-Crafts Reaction: RCOCl, AlCl 3 + R O R O RCOCl, AlCl 3 R O SiMe 3
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2 - Diels-Alder Reaction: R O + R R O + O major minor O + O + O major minor R R R O O O H OAc + O O O H OAc O O O H SPh + O O O H SPh OAc OAc Raney Ni, H 2 O O O H OAc Change in mechanism: R R R PhSH, H + SPh SPh PhSH, (PhCO 2 ) 2 Stereochemistry: Relative stereochemistry: Stereochemical relationship between two or more stereogenic centers within a molecule HO H H OH H H enantiomers same relative stereochemistry cholesterol syn:
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Selectivity - SELECTIVITY SELECTIVITY Science 1983, 219,...

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