Issue 28, 2024
From the journal:

Chemical Communications

Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals†

Dinesh Kumar Gopalakrishnan,a   Srashti Bhardwaj,a   Sandeep Kumar,a   Tarak Karmakar*a  and  Janakiram Vaitla ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, India
E-mail: tkarmakar@iitd.ac.in, vaitla@chemistry.iitd.ac.in

Abstract

The development of stereoselective olefination using sulfur ylide-derived vinyl carbenes with diazo esters and acetals is reported. Both reactions proceed through nucleophilic addition to electrophiles at the γ-position of an in situ-generated 2-alkoxy furan intermediate. The synthetic utility of the developed method is demonstrated by the total synthesis of rubrolide E. Detailed mechanistic investigations and quantum chemical calculations provide insight into the reaction mechanism.

Graphical abstract: Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals

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Article information

DOI
https://doi.org/10.1039/D4CC00450G
Article type
Communication
Submitted
30 Jan 2024
Accepted
07 Mar 2024
First published
18 Mar 2024

Chem. Commun., 2024,60, 3846-3849

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Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals

D. K. Gopalakrishnan, S. Bhardwaj, S. Kumar, T. Karmakar and J. Vaitla, Chem. Commun., 2024, 60, 3846 DOI: 10.1039/D4CC00450G

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