CC BY-NC-ND 4.0 · Synlett 2022; 33(01): 45-47
DOI: 10.1055/a-1695-4516
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A Chiral Sulfoxide-Based C–H Acid

Denis Höfler 
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany
,
Karl Kaupmees
b   University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu, Estonia
,
Ivo Leito
b   University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu, Estonia
,
Benjamin List  ∗
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany
› Author AffiliationsGenerous support by the European Research Council (Advanced Grant ‘C–H Acids for Organic Synthesis, CHAOS’) and the Deutsche Forschungsgemeinschaft (Leibniz Award to B.L. and Cluster of Excellence RESOLV, EXC 1069) is gratefully acknowledged. Work at Tartu was supported by the Estonian Research Council grant (PRG690), and by the EU through the European Regional Development Fund under project TK141 (2014-2020.4.01.15-0011).
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Abstract

We report the design and synthesis of a strong, chiral, enantiopure sulfoxide-based C–H acid. Single-crystal X-ray analysis confirms the proposed structure and its absolute configuration. The new motif shows a high acidity and activity in Brønsted and Lewis acid catalyzed transformations. So far, only little to no enantioselectivities were achieved.

Key words

sulfoxide C–H acids - stereogenic sulfur - triflyl groups - strong acids - noncoordinating anions - Brønsted acids

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1695-4516.
  • Supporting Information


Publication History

Received: 17 September 2021

Accepted after revision: 04 November 2021

Accepted Manuscript online:
12 November 2021

Article published online:
14 December 2021

© 2021. 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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