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CC BY-NC-ND 4.0 · Synlett 2023; 34(20): 2393-2395
DOI: 10.1055/a-2100-1575
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Special Issue Dedicated to Prof. Hisashi Yamamoto

Brønsted Acid Catalyzed Asymmetric Silylation of Biaryl Diols

Jung Tae Han
,
Hui Zhou
,
Benjamin List  ∗
Generous support from the Deutsche Forschungsgemeinschaft (Leibniz Award to B.L. and Germany’s Excellence Strategy–EXC 2033–390677874–RESOLV), and the European Research Council (European Union’s Horizon 2020 research and innovation program ‘Early Stage Organocatalysis, ESO’) is gratefully acknowledged.
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Abstract

We report a Brønsted acid catalyzed enantioselective silylation of biaryl diols with an allylsilane as a silicon source. This process enables facile access to enantioenriched biaryl silyl ethers with an axial stereogenicity. A control experiment supports a mechanism proceeding by desymmetrization followed by kinetic resolution.

Key words

Brønsted acid - imidodiphosphorimidate - silylation - axial chirality - desymmetrization - kinetic resolution

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2100-1575.
  • Supporting Information


Publication History

Received: 30 April 2023

Accepted after revision: 23 May 2023

Accepted Manuscript online:
25 May 2023

Article published online:
12 July 2023

© 2023 . This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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