A New Route for the Synthesis of Styrylbenzylsulfones, Precursors of 1-Benzylsulfonyl-2-Arylcyclopropanes

Reddy, M. V. Ramana; Reddy, D. Bhaskar; Reddy, P. V. R.; Vijayalaskhmi, S.

doi:10.1080/10426509008038037

Cited by 8 publications

(1 citation statement)

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“…Among the earliest examples, α,β-unsaturated sulfones have been demonstrated with nearly every type of condition disclosed thus far, ranging from the traditional NaH/DMSO conditions to soluble organic bases and even phase transfer conditions, all giving good to excellent yields (Table ). ,,, Like many of the electrophiles discussed thus far, these α,β-unsaturated sulfones are highly electrophilic with an E parameter of −24.69 for 49 . Examples in more complex structures, such as the cross-conjugated diene 143 and the heterocyclic sulfone 145 , have been demonstrated at gram scale (Scheme ).…”

Section: Reaction Scope and Limitationsmentioning

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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Section: Reaction Scope and Limitationsmentioning

confidence: 99%