Intramolecular anti-hydrosilylation and silicon-assisted cross-coupling: highly regio- and stereoselective synthesis of trisubstituted homoallylic alcohols |
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Authors: | Denmark Scott E Pan Weitao |
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Affiliation: | 245 Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA. denmark@scs.uiuc.edu |
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Abstract: | A highly regio- and stereoselective anti-intramolecular hydrosilylation of alkynyl silyl ethers catalyzed by a ruthenium arene complex has been developed. The resultant (Z)-alkylidenesilacyclopentanes are efficiently coupled with aryl or alkenyl halides in the presence of tetrabutylammonium fluoride and a palladium(0) catalyst. The yields are generally good, and the reaction is compatible with a wide range of functional groups. The overall transformation achieves the stereoselective conversion of homopropargyl alcohols to trisubstituted homoallylic alcohols. [reaction: see text] |
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