Facile synthesis of chiral [2,3]-fused hydrobenzofuran via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition

Chem Commun (Camb). 2019 Jan 3;55(4):553-556. doi: 10.1039/c8cc09226e.

Abstract

Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.