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Consecutive Ring-Expansion Reactions for the Iterative Assembly of Medium-Sized Rings and Macrocycles

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JournalSynlett
DateAccepted/In press - 26 Mar 2019
DateE-pub ahead of print - 12 Apr 2019
DatePublished (current) - 1 Jan 2020
Issue number2
Volume31
Number of pages14
Pages (from-to)133-146
Early online date12/04/19
Original languageEnglish

Abstract

Macrocycles and medium-sized rings have important applications in several scientific fields but can be challenging to make using traditional end-to-end cyclization reactions. Ring-expansion methods represent a useful alternative and offer numerous practical benefits. In this Account, we discuss the current state of the art of ring-expansion strategies that have been applied consecutively. Such methods have the power to expedite the design and synthesis of functionalized macro cycles via the selective, iterative insertion of smaller fragments into ring-enlarged products. 1 Introduction 2 Insertion Reactions 2.1 Transamidation/Transpeptidation 2.2 Transesterification 2.3 Transthioesterification 2.4 Aminyl Radical Cascade 2.5 Iterative Synthesis of Lactones 2.6 Successive Ring Expansion of β-Ketoesters and Lactams 3 Pericyclic Reactions 3.1 Sulfur-Mediated Rearrangements 3.2 Nitrogen-Mediated Rearrangements 4 Fragmentation Reactions 5 Conclusions and Future Outlook.

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© Georg Thieme Verlag. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

    Research areas

  • iterative synthesis, macro-cycles, medium-sized rings, rearrangements, ring enlargement, ring expansion

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