Reaction Pairing: A Diversity-Oriented Synthesis Strategy for the Synthesis of Diverse Benzofused Sultams

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Issue Date
2011-10-07Author
Samarakoon, Thiwanka Bandara
Loh, Joanna K.
Rolfe, Alan
Le, Lisa S.
Yoon, Sun Young
Lushington, Gerald H.
Hanson, Paul R.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol201962n.
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A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, SNAr addition and Mitsunobu alkylation) generating skeletally diverse benzofused tricyclic and bicyclic sultams is reported. Pairing sulfonylation and SNAr reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation–Mitsunobu–SNAr pairing allows access to benzo-oxathiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation–SNAr–Mitsunobu affords structurally different, benzofused bridged tricyclic sultams.
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Citation
Samarakoon, T. B., Loh, J. K., Rolfe, A., Le, L. S., Yoon, S. Y., Lushington, G. H., & Hanson, P. R. (2011). Reaction Pairing: A Diversity-Oriented Synthesis Strategy for the Synthesis of Diverse Benzofused Sultams. Organic Letters, 13(19), 5148–5151. http://doi.org/10.1021/ol201962n
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