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

View/ Open
Issue Date
2010-03-21Author
Samarakoon, Thiwanka Bandara
Hur, Moon Young
Kurtz, Ryan D.
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
Metadata
Show full item recordAbstract
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.
Collections
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
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.