A tandem annulation with a [1,3]-hydride transfer as the key step leading to isochromans

Yingwei Wang; Guangxun Li; Hongxin Liu; Zhuo Tang; Yuan Cao; Gang Zhao

doi:10.1039/c7cc06144g

A tandem annulation with a [1,3]-hydride transfer as the key step leading to isochromans

Chem Commun (Camb). 2017 Sep 26;53(77):10652-10655. doi: 10.1039/c7cc06144g.

Authors

Yingwei Wang¹, Guangxun Li, Hongxin Liu, Zhuo Tang, Yuan Cao, Gang Zhao

Affiliation

¹ Department of Pharmaceutical & Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu, Sichuan 610065, China. gzhao@scu.edu.cn.

PMID: 28905049
DOI: 10.1039/c7cc06144g

Abstract

An unprecedented method that enables the direct coupling of an α-C-H bond in alcohols with 2-arylacetaldehydes through a [1,3]-hydride transfer ([1,3]-HT) of oxocarbenium ions catalyzed by a Lewis acid has been developed. The redox neutral preparation of the isochroman derivatives proceeds via a tandem condensation/[1,3]-HT/Friedel-Crafts sequence with moderate to good yields. Deuterium-labeling studies provide mechanistic insights and reveal that the redox functionalization proceeds via a [1,3]-HT.