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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.
Samarakoon, Thiwanka Bandara
Loh, Joanna K.
Rolfe, Alan
Le, Lisa S.
Yoon, Sun Young
Lushington, Gerald H.
Hanson, Paul R.
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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.
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2011-10-07
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American Chemical Society
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Samarakoon_2011.pdf
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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