Journal
ORGANIC LETTERS
Volume 12, Issue 10, Pages 2182-2185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100495w
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Funding
- National Institute of General Medical Sciences [P41 GM076302]
- University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) [P50 GM069663]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0923449] Funding Source: National Science Foundation
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A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered 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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