Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer.
Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.
Department of Chemistry, New York University, New York, New York 10003, United States.
Margaret A
MA
Greene
Michel
M
Prévost
Joshua
J
Tolopilo
K A
KA
Woerpel
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D011090:Polyenes; D012821:Silanes; D012834:Silver