146539-22-2Relevant academic research and scientific papers
The Diastereoselectivity of Electrophilic Attack on Trigonal Carbon Adjacent to a Stereogenic Centre: Diastereoselective Protonation, Epoxidation and Acylation of Allylsilanes
Fleming, Ian,Lewis, Jeremy J.
, p. 3267 - 3276 (2007/10/02)
The four allylsilanes 6 and 8, which have a stereogenic centre carrying a phenyl group, a methyl group and a hydrogen atom adjacent to the nucleophilic end of the double bond, react with protic (or deuteronic) acid, m-chloroperbenzoic acid and chlorosulfonyl isocyanate to give eletrophilic substitution of the allylsilane, with diastereoselectivity in the sense 2, in conformity to a general rule for electrophilic attack on a double bond adjacent to a stereogenic centre.The most reliably stereoselective reactions took place with the allylsilane 6b, in which the stereogenic centre is cis to a group larger than a hydrogen atom in both the E- and Z-isomer.In general, chlorosulfonyl isocyanate induces higher stereoselectivity than the peracid, and the peracid higher stereoselectivity than the proton (or deuteron).
ANODIC SYNTHESIS OF BUTENOLIDES FROM β-ETHYLENIC ESTERS DOUBLE CYCLIZATION IN THE PRESENCE OF OLEFINS
Delaunay, J.,Orliac-Le Moing, A.,Simonet, J.
, p. 7089 - 7094 (2007/10/02)
Anodic oxidation of β-ethylenic esters yields butenolides 2.In the presence of 1-phenyl-1-propene or α,β-disubstituted indenones a double cyclization takes place to yield more complex butenolides
