Formal [4+3] Epoxide Cascade Reaction via a Complementary Ambiphilic Pairing Strategy

Rolfe, Alan; Samarakoon, Thiwanka Bandara; Hanson, Paul R.

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Issue Date

2010-03-19

Author

Rolfe, Alan

Samarakoon, Thiwanka Bandara

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/ol100035e

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Abstract

A formal [4+3] epoxide cascade protocol utilizing ambiphilic sulfonamides and a variety of epoxides (masked ambiphiles) has been developed for the generation of benzothiaoxazepine-1,1′-dioxides and oxathiazepine-1,1′-dioxides. This protocol combines an epoxide ring-opening with either an SNAr or oxa-Michael cyclization pathway.

Citation

Rolfe, A., Samarakoon, T. B., & Hanson, P. R. (2010). Formal [4+3] Epoxide Cascade Reaction via a Complementary Ambiphilic Pairing Strategy. Organic Letters, 12(6), 1216–1219. http://doi.org/10.1021/ol100035e

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