Riveiros Ricardo, Rodríguez David, Pérez Sestelo José, Sarandeses Luis A
Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain.
Org Lett. 2006 Mar 30;8(7):1403-6. doi: 10.1021/ol060192o.
[reaction: see text] Triorganoindium reagents (R(3)In) react with propargylic esters under palladium catalysis via an S(N)2' rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R(3)In (aryl, alkenyl, alkynyl, and methyl). When chiral, nonracemic propargylic esters are employed, the reaction takes place with high anti-stereoselectivity providing allenes with high enantiomeric excess.
[反应：见正文] 三有机铟试剂（R₃In）在钯催化下通过S(N)2'重排与炔丙基酯反应，以良好的产率和高区域选择性得到丙二烯。该反应在室温下能顺利进行，适用于多种R₃In（芳基、烯基、炔基和甲基）。当使用手性、非外消旋的炔丙基酯时，反应以高反式立体选择性进行，得到对映体过量值高的丙二烯。
