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

Samarakoon, Thiwanka Bandara
; 
Hur, Moon Young
; 
Kurtz, Ryan D.
; 
Hanson, Paul R.
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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.
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Date
2010-03-21
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American Chemical Society
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Chemistry Scholarly Works
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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
URI
https://hdl.handle.net/1808/23360
DOI
10.1021/ol100495w
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