Solvent Controlled\nChemodivergent Sulfonyl Addition\ninto Enynones: Synthesis of α‑Furyl Sulfones and Stereodefined\nVinyl Sulfones

Sodium\nsalt of aryl sulfinic acid reacts with enynone\nin a different\nmanner, yielding α-furyl sulfone and stereodefined vinyl sulfone\nin toluene and EtOH respectively in the presence of ZnCl<sub>2</sub>. The salient features of this protocol include chemoselectivity,\nbroad substrate scope, high efficiency, high yield, and easy purification.\nThe synthetic utilities of the products are demonstrated by cycloaddition\nand cis–trans photoisomerization reactions.

Publication Details

Journal
Figshare
Published
2024-12-28
DOI
https://doi.org/10.1021/acs.joc.4c02165.s001
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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0.00
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article

Solvent Controlled\nChemodivergent Sulfonyl Addition\ninto Enynones: Synthesis of α‑Furyl Sulfones and Stereodefined\nVinyl Sulfones

Figshare
Sulfur-Based Synthesis Techniques
article

Solvent Controlled\nChemodivergent Sulfonyl Addition\ninto Enynones: Synthesis of α‑Furyl Sulfones and Stereodefined\nVinyl Sulfones

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Abstract

Sodium\nsalt of aryl sulfinic acid reacts with enynone\nin a different\nmanner, yielding α-furyl sulfone and stereodefined vinyl sulfone\nin toluene and EtOH respectively in the presence of ZnCl<sub>2</sub>. The salient features of this protocol include chemoselectivity,\nbroad substrate scope, high efficiency, high yield, and easy purification.\nThe synthetic utilities of the products are demonstrated by cycloaddition\nand cis–trans photoisomerization reactions.

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Sulfur-Based Synthesis Techniques
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Solvent Controlled\nChemodivergent Sulfonyl Addition\ninto Enynones: Synthesis of α‑Furyl Sulfones and Stereodefined\nVinyl Sulfones · Figshare (2024) | TGRS Research Map | TGRS