Synthesis of Enantiopure 1,5-Enynes and 1,5-Diynes with Propargylic Quaternary Centers
作者:Ignacio Pérez、Francisco Yuste、Rubén Sánchez-Obregón、Rubén A. Toscano、José Alemán、Leyre Marzo、Ana M. Martín Castro、Inés Alonso、José Luis García Ruano
DOI:10.1002/ejoc.201500004
日期:2015.5
has been carried out with various allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. Desulfinylation of the resulting compounds with tBuLi provides access to enantiopure 1,5-enynes, 1,5-diynes, and 4-arylalkynes bearing all-carbon quaternary propargylic centers.
已经用各种烯丙基、炔丙基和苄基卤化物进行了邻亚磺酰基苄基-甲基炔丙基碳负离子的非对映选择性季铵化。立体选择性由亚磺酰基有效控制,作为远程手性助剂。用 tBuLi 对所得化合物进行脱硫酰化,可以得到对映体纯的 1,5-烯炔、1,5-二炔和 4-芳基炔烃,这些炔烃带有全碳季炔丙炔中心。