Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

• Published in: Synlett 2021-12, Vol.32 (19), p.1911-1933
• Main Authors: Benke, Zsanett, Nonn, Melinda, Remete, Attila M., Fustero, Santos, Kiss, Loránd
• Format: Article
• Language: English
• Subjects: account
• ISSN: 0936-5214; 1437-2096
• DOI: 10.1055/s-0040-1706041

Abstract This Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis. 1 Introduction 2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition 3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition 4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis 5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition 6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis 7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis 8 Summary and Outlook 9 List of Abbreviations