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. 2022 Jul 1;87(13):8796-8801.
doi: 10.1021/acs.joc.2c00770. Epub 2022 Jun 22.

Nickel-Catalyzed Tandem Ueno-Stork Cyclization: Stereoselective 1,2-Dicarbofunctionalization of Cyclic Alkenes

Pedro de Andrade Horn  1 , Hunter S Sims  1 , Mingji Dai  1
Affiliations

Nickel-Catalyzed Tandem Ueno-Stork Cyclization: Stereoselective 1,2-Dicarbofunctionalization of Cyclic Alkenes

Pedro de Andrade Horn et al. J Org Chem. .

Abstract

A nickel-catalyzed tandem Ueno-Stork cyclization is developed to enable stereoselective 1,2-dicarbofunctionalization of cyclic alkenes and efficiently build various bicyclic products. This new protocol does not involve any toxic or difficult-to-remove tin reagent and is scalable and amenable to build all-carbon quaternary centers.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Figure 1.
Figure 1.
Mechanistic study and proposed catalytic cycle
Scheme 1.
Scheme 1.
Ueno-Stork radical cyclization and its application
Scheme 2.
Scheme 2.
A. Derivatization studies and ORTEP diagram of 32 (ellipsoid contour probability level at 50%). B. Reaction scaleup.
See this image and copyright information in PMC

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