Stereochemistry of the reaction of Si-phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones.
Silenes generated through a silyl-modified Peterson olefination procedure can be trapped with a range of alkyl butadienes via a [4 + 2] cycloaddition pathway to afford silacycles accompanied by variable amounts of competing ene, [2 + 2] and silene dimer by-products. The silacycles are formed with good chemo- and stereo-selectivity and provide access to diols and lactones via a phenyl-triggered Fleming-Tamao oxidation.
Sanganee
Mahesh J
MJ
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK DH1 3LE.
Steel
Patrick G
PG
Whelligan
Daniel K
DK
D000215:Acylation; D002070:Butadienes / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D029751:Silene / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
D002070:Butadienes; D007783:Lactones; D012825:Silicon