Application of novel sulfonamides in enantioselective organocatalyzed cyclopropanation

Hartikka, Antti; Ślósarczyk, Adam T.; Arvidsson, Per I.

doi:10.1016/j.tetasy.2007.05.030

Cited by 48 publications

(9 citation statements)

References 21 publications

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“…Inspired by this work, Arvidsson and co-workers developed two new organocatalysts (leading to slightly improved selectivities) by replacing the carboxylic acid functionality with either a tetrazole or aryl sulfonamide group. , …”

Section: Sulfur Ylidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfur Ylidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…In 2007, Hartikka et al also described the enantioselective cyclopropanation of α,β-unsaturated aldehydes with sulfonium ylides by using newly developed chiral amine catalysts [Figure 6] [47,48] . With the tetrazolic acid functionalized dihydroindol C6 as the catalyst, chiral cyclopropanes 10 could be obtained in 99% ee for the seven examples [29] .…”

Section: Organocatalyzed Asymmetric Cyclopropanationmentioning

confidence: 99%

Application of sulfonium and sulfoxonium ylides in organocatalyzed asymmetric reaction

2023

Chem Synth

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Sulfur-based ylides are very important and valuable reagents in organic synthesis and have been widely applied in the preparation of cyclic compounds and the formation of C-X (X = C, N, O, S, B, P) bond. Since the early 2000s, asymmetric organocatalysis has become a powerful strategy in organic synthesis (even highlighted by the 2021 Nobel Prize in Chemistry) and has attracted widespread research interest among synthetic organic chemists. In this area, a large number of outstanding achievements have been registered in the novel chiral catalysts design, new compounds synthesis, various reagents application, and versatile reaction discovery. Given the extensive application of sulfonium and sulfoxonium ylides in organic synthesis, in this review, we mainly summarize the organocatalyzed asymmetric reactions involving these ylide reagents as one of the reactants. Detailed reaction mechanisms, transition states and some synthetic applications are highlighted. The challenges and opportunities of this field are also discussed in the outlook.

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“…The first involves iminium-ion catalysis with chiral pyrrolidine catalysts such as 347 and 348 (Scheme ). On account of the reaction mechanism, only α,β-unsaturated aldehydes can engage the catalyst. Good yields, high diastereoselectivity, and moderate to good enantioselectivity can be achieved with 3-alkyl- and 3-ayrl- E -disubstituted α,β-aldehyde acceptors.…”

Section: Selectivity: From Constitutional Isomers To Enantiomersmentioning

confidence: 99%

Opportunities for the Application and Advancement of the Corey–Chaykovsky Cyclopropanation

Beutner

George

2022

Org. Process Res. Dev.

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Cyclopropanes are a common motif in many pharmaceutically relevant compounds, and methods for the synthesis of these strained rings have relevance throughout the pharmaceutical development process. Among the many options, the Corey− Chaykovsky cyclopropanation stands out due to its broad substrate scope, high functional group tolerance, and mild conditions. Despite these benefits, its application to the synthesis of cyclopropanes, specifically in the context of large-scale syntheses, has been limited. In this review, the scope and limitations of the Brønsted-base-promoted Corey−Chaykovsky cyclopropanation with sulfur ylides will be examined. Through this discussion, gaps in the scope and understanding of the transformation will be highlighted to promote further application and advancement of this powerful and useful methodology.

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Application of novel sulfonamides in enantioselective organocatalyzed cyclopropanation

Cited by 48 publications

References 21 publications

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Application of sulfonium and sulfoxonium ylides in organocatalyzed asymmetric reaction

Opportunities for the Application and Advancement of the Corey–Chaykovsky Cyclopropanation

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