Organocatalytic Cycloaddition-elimination Cascade for Atroposelective Construction of Heterobiaryls

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Nov 25

PMID 34820108

Citations 5

Authors

Wen-Lei Xu

Wei-Ming Zhao

Ru-Xia Zhang

Jie Chen

Ling Zhou

Affiliations

Soon will be listed here.

Abstract

The first chiral phosphoric acid (CPA) catalyzed cycloaddition-elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing a highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities. The success of this strategy derives from the stepwise process involving CPA-catalyzed asymmetric formal [3 + 2] cycloaddition and subsequent central-to-axial chirality conversion by elimination of a carbamate. In addition, the practicality of this reaction had been verified by varieties of transformations towards functionalized atropisomers.

Citing Articles

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