Recent Applications and Trends in the Julia‐Kocienski Olefination

Abstract

The Julia-Kocienski (J-K) olefination is a modified version of Julia-Lythgoe olefination. In this reaction, an aldehyde or ketone is coupled with heterocycle-bearing sulfone in the presence of a strong base to yield alkene. It has shown wide application in the synthesis of olefinic fragments in natural product synthesis. The Julia-Kocienski olefination is one of the most efficient protocols for the synthesis of E-alkenes. Nowa-days, a variety of natural products were synthesised by using the Julia-Kocienski olefination as the key step, and several developments and modifications were witnessed in this area. This review comprehends the recent developments and achievements in Julia-Kocienski olefination along with its application in natural product synthesis covering literature from 2016 to 2021.

Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations

“…Among the most prevalent strategies for the construction of olefins is via the reaction of carbonyl compounds, including aldehydes and ketones, a process generally termed carbonyl olefination ( 1 ). Methods to achieve carbonyl olefination include several well-known “name reactions” such as the Wittig ( 2 , 3 ), Horner-Wadsworth-Emmons ( 4 , 5 ), Julia ( 6 , 7 ), Peterson ( 8 ), and Tebbe ( 9 ) olefinations (Fig. 1A).…”

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

“…The mechanistic aspects and the usefulness of Julia-Kocienski olefination reaction have been demonstrated in several reviews, book chapters and a recent tutorial review, [9][10][11][12][13][14][15][16][17][18][19] including more specialized accounts describing its application in the synthesis of natural products, [19,20] macrolides, [21] vitamin analogues [22] and fluorinated alkenes. [23] The scope and application of this olefination for other than aldehydes and ketones carbonyl compounds, i. e. carboxylic acid derivatives, via a twostep procedure were also recently reviewed.…”

“…In this article we focus on the exploitation of Julia‐Kocienski olefination in the synthesis of trisubstituted alkenes during the period 2016–2022. Anilkumar's review article [19] covers only partly this subject (some of the literature examples up to 2018) whereas other recent reviewing works [16,22,23c,24] cover in total a half dozen of the examples presented herein. The examples for the different carbonyl partners have been reviewed separately whereas further organization was adopted in certain subcategories (all‐carbon or halogen substituted targets and classification depending on the main aim of the presented work).…”

Stereoselective synthesis of vinyl nitriles through a Ramberg–Bäcklund approach

“…Classic olefination reactions, such as the Wittig, 1 Julia–Kocienski, 2 Horner–Wadsworth–Emmons, 3 and Peterson reactions, 4 require two complementary reactants with reaction-specific functional groups: a nucleophile (such as phosphorus, sulfonyl, phosphonate, or silicon ylides) and a carbonyl electrophile. In contrast, the Meyer modification 5 of the Ramberg–Bäcklund reaction (RBR) 6 only requires a sulfonyl group that is flanked by two activated C–H bonds (such as methyl, methylene, or methine).…”