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Aranha RM, Bowser AM, Madalengoitia JS. Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene. Org Lett. 2009;11(3):575-8doi: 10.1021/ol802577z.
Aranha, R. M., Bowser, A. M., & Madalengoitia, J. S. (2009). Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene. Organic letters, 11(3), 575-8. https://doi.org/10.1021/ol802577z
Aranha, Rachel M, et al. "Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene." Organic letters vol. 11,3 (2009): 575-8. doi: https://doi.org/10.1021/ol802577z
Aranha RM, Bowser AM, Madalengoitia JS. Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene. Org Lett. 2009 Feb 05;11(3):575-8. doi: 10.1021/ol802577z. PMID: 19125576.
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Org Lett. 2009 Feb 05;11(3):575-8. doi: 10.1021/ol802577z.

Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene.

Organic letters

Rachel M Aranha, Amy M Bowser, Jose S Madalengoitia

Affiliations

  1. Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.

PMID: 19125576 DOI: 10.1021/ol802577z

Abstract

Tertiary allylic amines with an electron-deficient alkene react with isocyanates and isothiocyanates to give highly substituted ureas and thioureas arising from formal 1,3-diaza-Claisen rearrangements. Isocyanates and isothiocyanates with strong electron-withdrawing groups are more reactive. Similarly, the data suggest that a stronger electron-withdrawing substituent on the alkene favors a faster reaction, but this may be offset by sterics in the cyclic transition state.

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