Davenport Research Laboratories, Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.
Org Lett. 2018 Mar 2;20(5):1380-1383. doi: 10.1021/acs.orglett.8b00153. Epub 2018 Feb 9.
A rhodium-catalyzed conjugate alkynylation/aldol cyclization cascade was developed. Densely functionalized cyclic α-propargyl-β-hydroxyketones were synthesized with simultaneous formation of a C(sp)-C(sp) bond, a C(sp)-C(sp) bond, as well as three new contiguous stereocenters. The transformation was achieved with excellent enantio- and diastereoselectivities using BINAP as the ligand. The synthetic utility of the newly installed alkynyl moiety was exhibited by subjecting the products to an array of derivatizations.
发展了一种铑催化的共轭炔基化/醛醇环化级联反应。通过同时形成 C(sp)-C(sp)键、C(sp)-C(sp)键以及三个新的连续立体中心，合成了具有密集官能团的环状α-丙炔基-β-羟基酮。该转化使用 BINAP 作为配体，以优异的对映选择性和非对映选择性实现。通过对产物进行一系列衍生化反应，展示了新引入的炔基部分的合成实用性。
