%0 Journal Article %A O'Hora, Paul %A Incerti-Pradillos, Celia A. %A Kabeshov, Mikhail A. %A Shipilovskikh, Sergei A. %A Rubtsov, Aleksandr E. %A Elsegood, Mark %A Malkov, Andrei %D 2015 %T Catalytic asymmetric crotylation of aldehydes: application in total synthesis of (−)‐elisabethadione %U https://repository.lboro.ac.uk/articles/journal_contribution/Catalytic_asymmetric_crotylation_of_aldehydes_application_in_total_synthesis_of__elisabethadione/9394031 %2 https://repository.lboro.ac.uk/ndownloader/files/17008499 %K Allylation %K Asymmetric catalysis %K Rearrangement %K Stereoselectivity %K Total synthesis %K Chemical Sciences not elsewhere classified %X A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (À)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries. %I Loughborough University