Highly Stereoselective Synthesis of Multisubstituted Olefins from Alkynyl Tetracoordinate Borons and Iodonium Ylides via a Cyclic Intermediate
Jinchao Liang, Xin Chen, Jinglong Chen, Xingxing Ma, Qiuling Song
Abstract
We developed an intriguing and practical strategy for highly stereoselective assembly of multisubstituted olefins from alkynyl tetracoordinate boron species via a cyclic intermediate with 1,2-phenyl migration. We also developed a general method for the construction of deuterated trisubstituted alkenes from a cheap deuteration source, D 2 O, and the corresponding deuterated trisubstituted alkenes were obtained with excellent deuteration rates. This transformation features a novel reaction mechanism, exclusive stereoselectivity, and deuterated trisubstituted alkenes with excellent deuteration ratios.
Topics & Concepts
TetracoordinateStereoselectivityChemistryDeuteriumOrganoboron compoundsBoronStereochemistryOrganic chemistryCombinatorial chemistryCatalysisPlanarPhysicsComputer scienceComputer graphics (images)Quantum mechanicsAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis