Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer.

ABSTRACT: 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.

SUBMITTER: Greene MA 

PROVIDER: S-EPMC3437758 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature