50871-04-0Relevant academic research and scientific papers
Regioselective cross-coupling of allylindium reagents with activated benzylic bromides-a simple and efficient procedure for the synthesis of terminal alkenes
Ranu, Brindaban C.,Banerjee, Subhash,Adak, Laksmikanta
, p. 7374 - 7379 (2008/03/13)
Allylindium reagents undergo facile and highly regioselective cross-coupling with benzylic and cinnamyl bromides in THF at room temperature without any catalyst producing terminal alkenes in high yields. The addition is highly regioselective and is found to provide γ-adducts in all reactions.
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).
STEUERUNG DER REGIOSELEKTIVITAET BEI DER ADDITION VON BUT-2-ENYLZINK-VERBINDUNGEN AN STYROL
Lehmkuhl, Herbert,Nehl, Hans
, p. 131 - 136 (2007/10/02)
The addition of the butenyl-zinc bond in CH3CH=CHCH2ZnX derivatives VI-XII (X=n-C4H9, t-C4H9, Ph, cyclohexyl, Cl, OCH3, OPh) to styrene (XIII) affords a mixture of Zn -> Cprim and Zn -> Csec products.The regioselectivity can be contr
