A Formal [4+4] Complementary Ambiphile Pairing (CAP) Reaction: A New Cyclization Pathway for ortho-Quinone Methides

Samarakoon, Thiwanka Bandara; Hur, Moon Y.; Kurtz, Ryan; Hanson, Paul R.

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Issue Date

2010-03-21

Author

Samarakoon, Thiwanka Bandara

Hur, Moon Y.

Kurtz, Ryan

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/ol100495w

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Abstract

A formal, one-pot, [4+4] cyclization pathway for the generation of 8-member sultams via in-situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in-situ-generated o-QM in a formal [4+4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4+4] cyclization.

Citation

Samarakoon, T. B., Hur, M. Y., Kurtz, R. D., & Hanson, P. R. (2010). A Formal [4+4] Complementary Ambiphile Pairing (CAP) Reaction: A New Cyclization Pathway for ortho-Quinone Methides. Organic Letters, 12(10), 2182–2185. http://doi.org/10.1021/ol100495w

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