Asymmetric Halocyclizations of 2-Vinylbenzyl Alcohols with Chiral FLPs
Caifang Han, Xiangqing Feng, Haifeng Du
Abstract
By the use of a chiral frustrated Lewis pair (FLP) consisting of a chiral-diene-derived borane and tBu3P as the catalyst, an asymmetric halocyclization of 2-vinylbenzyl alcohols with NBS or NIS was successfully realized. A variety of optically active 1,3-dihydroisobenofuran derivatives were obtained in high yields with up to 87% ee and could be conveniently converted to other useful chiral compounds.
Topics & Concepts
ChemistryFrustrated Lewis pairBoraneCatalysisEnantioselective synthesisOrganic chemistryOptically activeAsymmetric hydrogenationCombinatorial chemistryLewis acids and basesOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisChemical Synthesis and Reactions