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Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines

Zachary J. Garlets, Mattia Silvi and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email: jpwolfeumich.edu

Z. J. Garlets, M. Silvi, J. P. Wolfe, Org. Lett., 2016, 18, 2331-2334.

DOI: 10.1021/acs.orglett.6b00598 (free Supporting Information)


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Abstract

A silver-catalyzed hydroamination of tosyl-protected N-allylguanidines provides substituted cyclic guanidines in high yields. The reactions can be used for construction of quaternary stereocenters as well as both monocyclic and bicyclic guanidine products.

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Key Words

guanidines, N-heterocyles, oxygen


ID: J54-Y2016