Intramolecular anti-hydrosilylation and silicon-assisted cross-coupling: highly regio- and stereoselective synthesis of trisubstituted homoallylic alcohols.
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]
Denmark
Scott E
SE
245 Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA. denmark@scs.uiuc.edu
Pan
Weitao
W
D008958:Models, Molecular; D008968:Molecular Conformation; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry*; D012825:Silicon; D013329:Structure-Activity Relationship
D020005:Propanols; C006463:allyl alcohol; D012825:Silicon