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

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