Enantioselective synthesis of axially chiral 1,2'-binaphthyls via nickel-catalyzed asymmetric [2+4] annulation
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Enantioselective synthesis of axially chiral 1,2'-binaphthyls via nickel-catalyzed asymmetric [2+4] annulation

Weitao Hu
,
Yujia Mao
,
Chuan Wang
*
*Correspondence to: Chuan Wang, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei 230026, Anhui, China. E-mail: chuanw@ustc.edu.cn
Chiral Chem. 2026;2:202619. 10.70401/cc.2026.0031
Received: April 05, 2026Accepted: June 15, 2026Published: June 16, 2026
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This manuscript is made available in its unedited form to allow early access to the reported findings. Further editing will be completed before final publication. As such, the content may include errors, and standard legal disclaimers are applicable.

Abstract

Axially chiral biaryls exhibit broad applications across diverse disciplines, and thus the development of conceptually new methods for accessing this structural motif remains highly desirable. Herein, we report the successful implementation of atroposelective de novo benzene formation via asymmetric [2+4] annulation in the enantioselective synthesis of axially chiral 1,2'-binaphthyls using β-substituted α-naphthylalkynes and o-iodostyrenes as C-4 and C-2 synthons, respectively. This nickel/PyrOX-catalyzed annulation reaction features a broad substrate scope (43 examples), excellent regiocontrol, exclusive 6-endo cyclization, and good to high enantioselectivity (up to 92% ee). Furthermore, the synthetic utility of the products is demonstrated through their efficient derivatizations into a range of potential bidentate ligands and bifunctional organocatalysts.

Keywords

Annulation, nickel, atropisomer, binaphthyl, asymmetric synthesis

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Hu W, Mao Y, Wang C. Enantioselective synthesis of axially chiral 1,2'-binaphthyls via nickel-catalyzed asymmetric [2+4] annulation. Chiral Chem. 2026;2:202619. https://doi.org/10.70401/cc.2026.0031

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