Review
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Latest Developments in the Julia-Kocienski Olefination Reaction: Mechanistic Considerations
Version 1
: Received: 11 May 2024 / Approved: 11 May 2024 / Online: 13 May 2024 (08:13:11 CEST)
A peer-reviewed article of this Preprint also exists.
Chrenko, D.; Pospíšil, J. Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations. Molecules 2024, 29, 2719. Chrenko, D.; Pospíšil, J. Latest Developments of the Julia–Kocienski Olefination Reaction: Mechanistic Considerations. Molecules 2024, 29, 2719.
Abstract
The Julia-Kocienski olefination reaction has become over past 30 years since its discovery one of the key C-C connective methods that is used in the late-stage natural product synthesis. The reaction proceeds under mild reaction conditions, with wide substrate scope and functional group tolerance, and with high (E) selectivity. In this 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
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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