Literature DB >> 20394415

A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.

Thiwanka B Samarakoon1, Moon Y Hur, Ryan D Kurtz, Paul R Hanson.   

Abstract

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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Year:  2010        PMID： 20394415      PMCID： PMC2888001          DOI： 10.1021/ol100495w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


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