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

Zsanett Benke; Melinda Nonn; Attila M. Remete; Santos Fustero; Loránd Kiss

doi:10.1055/s-0040-1706041

Synlett, Table of Contents

Synlett 2021; 32(19): 1911-1933
DOI: 10.1055/s-0040-1706041

account

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

Authors

Zsanett Benke

^aInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

^bUniversity of Szeged, Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, Eötvös u. 6, 6720 Szeged, Hungary
Melinda Nonn

^aInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

^bUniversity of Szeged, Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, Eötvös u. 6, 6720 Szeged, Hungary
Attila M. Remete

^aInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

^bUniversity of Szeged, Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, Eötvös u. 6, 6720 Szeged, Hungary
Santos Fustero

^cDepartment of Organic Chemistry, University of Valencia, Pharmacy Faculty, 46100 Burjassot Valencia, Spain
Loránd Kiss∗

^aInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

^bUniversity of Szeged, Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, Eötvös u. 6, 6720 Szeged, Hungary

Abstract

All articles of this category

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

Key words

metathesis - selectivity - β-lactam - isoxazoline - fluorine

Full Text

References

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