Literature DB >> 33274788

Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes.

Alexander Sandvoß1,2, Johannes M Wiest1,2.   

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.
© 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Entities:  

Keywords:  asymmetric synthesis; desymmetrization; oxetane; oxygen heterocycles; strained molecules

Year:  2021        PMID: 33274788     DOI: 10.1002/chem.202004923

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

1.  Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.

Authors:  Juan J Rojas; Elena Torrisi; Maryne A J Dubois; Riashat Hossain; Andrew J P White; Giovanni Zappia; James J Mousseau; Chulho Choi; James A Bull
Journal:  Org Lett       Date:  2022-03-21       Impact factor: 6.005

2.  Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.

Authors:  Alexander Sandvoß; Henning Maag; Constantin G Daniliuc; Dieter Schollmeyer; Johannes M Wahl
Journal:  Chem Sci       Date:  2022-05-04       Impact factor: 9.969

3.  Unexpected Isomerization of Oxetane-Carboxylic Acids.

Authors:  Bohdan Chalyk; Anastasiia Grynyova; Kateryna Filimonova; Tymofii V Rudenko; Dmitry Dibchak; Pavel K Mykhailiuk
Journal:  Org Lett       Date:  2022-06-29       Impact factor: 6.072

4.  Bioinspired Cobalt-Catalysis Enables Generation of Nucleophilic Radicals from Oxetanes.

Authors:  Aleksandra Potrząsaj; Michał Ociepa; Wojciech Chaładaj; Dorota Gryko
Journal:  Org Lett       Date:  2022-03-25       Impact factor: 6.005

  4 in total

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