Intramolecular vinylsilane-oxocarbenium condensations: concise assembly of cis-bicyclic ether arrays.
Lewis acid-mediated intramolecular attack of vinylsilanes at tethered oxonium precursors 1 results in a rapid assembly of the cis-fused bicyclic ether species 3, with complete regio- and stereospecific control, and in some cases near-quantitative yield. Continued investigation suggests a general approach to a variety of such ether frameworks.
Fearnley
Stephen Philip
SP
Department of Chemistry & Physics, Lamar University, P.O. Box 10022, Beaumont, Texas 77710, USA. fearnley@york.cuny.edu
Lory
Pedro
P
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D001643:Bridged Bicyclo Compounds; D004988:Ethers, Cyclic; D012821:Silanes; D014753:Vinyl Compounds; C476909:vinylsilane; D010100:Oxygen