Nazarov Cyclization and Tandem [4 + 2]-Cycloaddition Reactions of Donor–Acceptor Cyclopropanes

The development of aryl vinyl/divinyl donor–acceptor cyclopropanes (DACs) as novel Nazarov cyclization (NC) precursors is described. The 1,3-zwitterion, generated from DACs embedded in the divinyl framework, acts as a pentadienyl cation, a requisite for Nazarov cyclization. A cyclic allyl cation in...

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Bibliographic Details
Published in:Organic letters 2017-09, Vol.19 (17), p.4500-4503
Main Authors: Sudhakar, Gangarajula, Mahesh, S. K, Vemulapalli, S. Phani Babu, Nanubolu, Jagadeesh Babu
Format: Article
Language:English
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Summary:The development of aryl vinyl/divinyl donor–acceptor cyclopropanes (DACs) as novel Nazarov cyclization (NC) precursors is described. The 1,3-zwitterion, generated from DACs embedded in the divinyl framework, acts as a pentadienyl cation, a requisite for Nazarov cyclization. A cyclic allyl cation in the course of NC was trapped with external nucleophiles to provide an interrupted NC product. Indeed, an allyl cation in this reaction is analogous to a 1,4-zwitterion that on reaction with dipolarophiles provided an easy access to substituted pyrans with excellent yield and diastereoselectivity via NC followed by a formal [4 + 2] cycloaddition.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02061