Dynamic catalytic highly enantioselective 1,3‐dipolar cycloadditions

Yildirim, O., Grigalunas, M., Brieger, L., Strohmann, C., Antonchick, A.P. ORCID: 0000-0003-0435-9443 and Waldmann, H., 2021. Dynamic catalytic highly enantioselective 1,3‐dipolar cycloadditions. Angewandte Chemie, 133 (36), pp. 20165-20173. ISSN 0044-8249

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Abstract

In dynamic covalent chemistry, reactions follow a thermodynamically controlled pathway through equilibria. Reversible covalent-bond formation and breaking in a dynamic process enables the interconversion of products formed under kinetic control to thermodynamically more stable isomers. Notably, enantioselective catalysis of dynamic transformations has not been reported and applied in complex molecule synthesis. We describe the discovery of dynamic covalent enantioselective metal-complex-catalyzed 1,3-dipolar cycloaddition reactions. We have developed a stereodivergent tandem synthesis of structurally and stereochemically complex molecules that generates eight stereocenters with high diastereo- and enantioselectivity through asymmetric reversible bond formation in a dynamic process in two consecutive Ag-catalyzed 1,3-dipolar cycloadditions of azomethine ylides with electron-poor olefins. Time-dependent reversible dynamic covalent-bond formation gives enantiodivergent and diastereodivergent access to structurally complex double cycloadducts with high selectivity from a common set of reagents.

Item Type: Journal article
Description: Simultaneously published in the international version of the journal:
Angewandte Chemie International Edition, 60(36), 20012-20020, September 2021. DOI: 10.1002/anie.202108072
Publication Title: Angewandte Chemie
Creators: Yildirim, O., Grigalunas, M., Brieger, L., Strohmann, C., Antonchick, A.P. and Waldmann, H.
Publisher: Wiley
Date: September 2021
Volume: 133
Number: 36
ISSN: 0044-8249
Identifiers:
NumberType
10.1002/ange.202108072DOI
1526729Other
Rights: © 2021 The Authors. Angewandte Chemie published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Divisions: Schools > School of Science and Technology
Record created by: Laura Ward
Date Added: 18 Mar 2022 09:59
Last Modified: 18 Mar 2022 09:59
Related URLs:
URI: http://irep.ntu.ac.uk/id/eprint/45912

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