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Review

Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations

by
Daniel Chrenko
1 and
Jiří Pospíšil
1,2,3,*
1
Department of Chemical Biology, Faculty of Science, Palacky University, Šlechtitelů 27, 779 00 Olomouc, Czech Republic
2
Department of Organic Chemistry, Faculty of Science, Palacky University, 17. Listopadu, 779 00 Olomouc, Czech Republic
3
Laboratory of Growth Regulators, Palacky University & Institute of Experimental Botany AS CR, Šlechtitelů 27, 779 00 Olomouc, Czech Republic
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(12), 2719; https://doi.org/10.3390/molecules29122719
Submission received: 10 May 2024 / Revised: 30 May 2024 / Accepted: 3 June 2024 / Published: 7 June 2024
(This article belongs to the Section Organic Chemistry)
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Abstract

Since its discovery, the Julia–Kocienski olefination reaction has over past 30 years become one of the key C-C connective methods that is used in late-stage natural product synthesis. The reaction proceeds under mild reaction conditions, with a wide substrate scope and functional group tolerance range and with high (E) selectivity. In this focused review, we discuss the reaction from a mechanistic point of view and disclose key features that play an important role in reaction selectivity. Finally, the mechanistic aspects of the newly developed modification of the Julia–Kocienski reaction, which allows the formation of both (E) and (Z) olefins from the same reaction partners, are discussed.
Keywords: Julia–Kocienski reaction; olefination; reaction selectivity; reaction mechanism Julia–Kocienski reaction; olefination; reaction selectivity; reaction mechanism

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MDPI and ACS Style

Chrenko, D.; Pospíšil, J. Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations. Molecules 2024, 29, 2719. https://doi.org/10.3390/molecules29122719

AMA Style

Chrenko D, Pospíšil J. Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations. Molecules. 2024; 29(12):2719. https://doi.org/10.3390/molecules29122719

Chicago/Turabian Style

Chrenko, Daniel, and Jiří Pospíšil. 2024. "Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations" Molecules 29, no. 12: 2719. https://doi.org/10.3390/molecules29122719

APA Style

Chrenko, D., & Pospíšil, J. (2024). Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations. Molecules, 29(12), 2719. https://doi.org/10.3390/molecules29122719

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