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

Samarakoon, Thiwanka Bandara; Loh, Joanna K.; Rolfe, Alan; Le, Lisa S.; Yoon, Sun Young; Lushington, Gerald H.; Hanson, Paul R.

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Issue Date

2011-10-07

Author

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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Abstract

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.

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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