Enantioselective Synthesis of C�O Axially Chiral Diaryl Ethers by NHC-Catalyzed Atroposelective Desymmetrization**

Shee, S and Shree Ranganathappa, S and Gadhave, MS and Gogoi, R and Biju, AT (2023) Enantioselective Synthesis of C�O Axially Chiral Diaryl Ethers by NHC-Catalyzed Atroposelective Desymmetrization**. In: Angewandte Chemie - International Edition, 62 (52).

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Abstract

Axially chiral diaryl ethers, a distinguished class of atropisomers possessing unique dual C�O axis, hold immense potential for diverse research domains. In contrast to the catalytic enantioselective synthesis of conventional single axis bearing atropisomers, the atroposelective synthesis of axially chiral ethers containing flexible C�O axis remains a significant challenge. Herein, we demonstrate the first N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. Mechanistically, the reaction proceeds via NHC-catalyzed desymmetrization strategy to afford the corresponding axially chiral diaryl ether atropisomers in good yields and high enantioselectivities under mild conditions. The derivatization of the synthesized product expands the utility of present strategy via access to a library of C�O axially chiral compounds. The temperature dependency and preliminary investigations on the racemization barrier of C�O bonds are also presented. © 2023 Wiley-VCH GmbH.

Item Type:	Journal Article
Publication:	Angewandte Chemie - International Edition
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc.
Keywords:	C (programming language); Catalysis; Enantioselectivity; Synthesis (chemical), Atropisomers; Axially chiral diaryl ether; Desym-metrization; Diaryl ethers; Dual axis; Dual-axis chirality; Enantioselective synthesis; N-heterocyclic carbenes; Organocatalysis; Research domains, Ethers
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	01 Mar 2024 05:50
Last Modified:	01 Mar 2024 05:50
URI:	https://eprints.iisc.ac.in/id/eprint/83832

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