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Synlett 2021; 32(19): 1911-1933
DOI: 10.1055/s-0040-1706041
DOI: 10.1055/s-0040-1706041
account
Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction
We are grateful to the Hungarian Research Foundation (NKFIH K 119282 and FK 134586) for financial support. The financial support of the GINOP-2.3.2-15-2016-00014 project is also acknowledged. This research was supported by the EU-funded Hungarian grant (EFOP-3.6.1-16-2016-00008). Ministry of Human Capacities, Hungary (20391-3/2018/FEKUSTRAT) is also acknowledged. This work was supported by the New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund (ÚNKP-20-3).
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
Publication History
Received: 17 April 2021
Accepted after revision: 27 April 2021
Article published online:
19 May 2021
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