Department of Organic Chemistry, Stockholm University, Sweden.
Department of Materials and Environmental Chemistry, Stockholm University, Sweden.
Angew Chem Int Ed Engl. 2016 Nov 7;55(46):14417-14421. doi: 10.1002/anie.201608605. Epub 2016 Oct 13.
The catalytic asymmetric allylboration of cyclic imines with γ,γ-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.
γ,γ-二取代烯丙基硼酸与环状亚胺的催化不对称烯丙基硼化反应以高产率和立体选择性提供具有相邻立体中心的产物。通过切换烯丙基硼酸酯的 E/Z 几何形状和/或 BINOL 催化剂的对映异构体，可以以完全立体发散的方式对各种亲电试剂（包括 3,4-二氢异喹啉和吲哚）进行prenylation。在一步合成中，3-甲基吲哚以高立体选择性提供具有三个相邻立体中心的产物。
