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. 2014 Jul 7;20(28):8782-90.
doi: 10.1002/chem.201402258. Epub 2014 Jun 17.

Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides

Ryan M Fornwald  1 , Jonathan A Fritz, John P Wolfe
Affiliations

Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides

Ryan M Fornwald et al. Chemistry. .

Abstract

The Pd-catalyzed coupling of N-allylsulfamides with aryl and alkenyl triflates to afford cyclic sulfamide products is described. In contrast to other known Pd-catalyzed alkene carboamination reactions, these transformations may be selectively induced to occur by way of either anti- or syn-aminopalladation mechanistic pathways by modifying the catalyst structure and reaction conditions.

Keywords: addition reactions; alkenes; heterocycles; palladium; stereoselectivity.

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Figures

Scheme 1
Scheme 1
Syn Aminopalladation Mechanism
Scheme 2
Scheme 2
Anti-aminopalladation mechanism
See this image and copyright information in PMC

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