Synthesis of Enantiopure 1,5-Enynes and 1,5-Diynes with Propargylic Quaternary Centers (pages 3314–3319)
Ignacio Pérez, Francisco Yuste, Rubén Sánchez-Obregón, Rubén A. Toscano, José Alemán, Leyre Marzo, Ana M. Martín Castro, Inés Alonso and José Luis García Ruano
Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500004
Diastereoselective quaternization of o-sulfinylbenzyl-methylpropargylic carbanions has been achieved with allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. This method provides access to enantiopure 1,5-enynes, 1,5-diynes, and 4-arylalkynes bearing quaternary propargylic centers.