Latest Developments of the Julia-Kocienski Olefination Reaction: Mechanistic Considerations.

Molecules

Department of Chemical Biology, Faculty of Science, Palacky University, Šlechtitelů 27, 779 00 Olomouc, Czech Republic.

Published: June 2024

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 () 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 () and () olefins from the same reaction partners, are discussed.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11206144PMC
http://dx.doi.org/10.3390/molecules29122719DOI Listing

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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 () 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.

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