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      Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes

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          Abstract

          Strain relief of oxetanes offers a plethora of opportunities for the synthesis of chiral alcohols and ethers. In this context, enantioselective desymmetrization has been identified as a powerful tool to construct molecular complexity and this has led to the development of elegant strategies on the basis of transition metal, Lewis acid, and Brønsted acid catalysis. This review highlights recent examples that harness the inherent reactivity of prochiral oxetanes and offers an outlook on the immense possibilities for synthetic application.

          Abstract

          Prochiral oxetanes are excellent candidates for the synthesis of chiral alcohols and ethers via enantioselective desymmetrization. Recent methods relying on transition metal, Lewis acid, and Brønsted acid catalysis allow access to a remarkably diverse set of compounds, which are highlighted and put into context.

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          Comprehensive Heterocyclic Chemistry III, Vol. 8

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            Author and article information

            Contributors
            wiest@uni-mainz.de
            Journal
            Chemistry
            Chemistry
            10.1002/(ISSN)1521-3765
            CHEM
            Chemistry (Weinheim an Der Bergstrasse, Germany)
            John Wiley and Sons Inc. (Hoboken )
            0947-6539
            1521-3765
            02 February 2021
            01 April 2021
            : 27
            : 19 ( doiID: 10.1002/chem.v27.19 )
            : 5871-5879
            Affiliations
            [ 1 ] Department Chemie Johannes Gutenberg Universität Mainz Duesbergweg 10–14 55128 Mainz Germany
            [ 2 ] Organisch-Chemisches Institut Westfälische Wilhelms-Universität Münster Corrensstrasse 36 48149 Münster Germany
            Author information
            http://orcid.org/0000-0002-2456-5597
            http://orcid.org/0000-0001-8284-3965
            Article
            CHEM202004923
            10.1002/chem.202004923
            8049043
            33274788
            6ba43a4c-e651-484b-b07e-be33668f9825
            © 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH

            This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

            History
            : 11 November 2020
            Page count
            Figures: 17, Tables: 0, References: 139, Pages: 9, Words: 0
            Funding
            Funded by: Verband der Chemischen Industrie , open-funder-registry 10.13039/100007215;
            Award ID: Liebig
            Funded by: Studienstiftung des Deutschen Volkes , open-funder-registry 10.13039/501100004350;
            Award ID: PhD fellowship
            Categories
            Minireview
            Minireviews
            Asymmetric Synthesis
            Custom metadata
            2.0
            April 1, 2021
            Converter:WILEY_ML3GV2_TO_JATSPMC version:6.0.2 mode:remove_FC converted:15.04.2021

            Chemistry
            asymmetric synthesis,desymmetrization,oxetane,oxygen heterocycles,strained molecules
            Chemistry
            asymmetric synthesis, desymmetrization, oxetane, oxygen heterocycles, strained molecules

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