Hydroxy- and carboxy-substituted allylsilanes. A simple and stereoselective method of preparation
When treated with 2 equiv of a BuLi/KOCMe3 mixt., terminal olefins carrying unprotected OH or CO2H groups generate allylmetal intermediates which are trapped with Me3SiCl to afford functionalized (Z-2-alkenyl)trimethylsilanes. E.g., treating CH2:CHMeCO2H with 2 equiv BuLi/KOCMe3 in THF followed by Me3SiCl gave 52% E-Me3SiCH2CH:CMeCO2H. One equivalent of the superbasic reagent suffices if the unsatd. alcs. are first protected as acetals before being subjected to the metalation/silylation/hydrolysis sequence. [on SciFinder (R)]
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CAN 126:238415 29-6 Organometallic and Organometalloidal Compounds Institut Chimie Organique,Universite Lausanne,Lausanne,Switz. Journal written in English. 188531-53-5P; 188531-54-6P; 188531-55-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis; stereoselective synthesis of hydroxy and carboxy allylsilanes); 75-77-4 (Chlorotrimethylsilane); 106-22-9 (Citronellol); 109-92-2; 112-43-6 (10-Undecen-1-ol); 1569-60-4 (6-Methyl-5-hepten-2-ol); 6090-15-9 (2,6-Dimethyl-5-hepten-2-ol); 13175-44-5 (7-Octen-1-ol); 53774-20-2 (2-Methyl-3-butenoic acid); 89794-36-5 (5-Hepten-1-ol); 140226-68-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective synthesis of hydroxy and carboxy allylsilanes); 97997-91-6P; 188531-45-5P; 188531-46-6P; 188531-51-3P; 188531-56-8P; 188531-58-0P; 188531-60-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective synthesis of hydroxy and carboxy allylsilanes); 188531-47-7P; 188531-48-8P; 188531-49-9P; 188531-50-2P; 188531-52-4P; 188531-57-9P; 188531-59-1P; 188531-61-5P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective synthesis of hydroxy and carboxy allylsilanes)
REVIEWED
EPFL