Organic Letters
Organic Letters
5 years ago

Intramolecular Formation of Zwitterionic Intermediates in 1,3-Diaza-Claisen Rearrangements

Intramolecular Formation of Zwitterionic Intermediates in 1,3-Diaza-Claisen Rearrangements
Rebecca Watson, Stevenson Flemer, Joel D. Walker, Yanbo Yang, José S. Madalengoitia
Isothioureas tethered to bridged-bicyclic tertiary allylic amines can be converted to carbodiimides through reaction with Hg(II) salts. Intramolecular cyclization of the tethered tertiary allylic amines to the carbodiimides afford zwitterionic intermediates that undergo 1,3-diaza-Claisen rearrangements, affording highly substituted tricyclic guanidines.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01746

DOI: 10.1021/acs.orglett.7b01746

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