Organic Letters
Organic Letters
5 years ago

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

Nazarov Cyclization and Tandem [4 + 2]-Cycloaddition Reactions of Donor–Acceptor Cyclopropanes
S. Phani Babu Vemulapalli, Gangarajula Sudhakar, S. K. Mahesh, Jagadeesh Babu Nanubolu
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02061

DOI: 10.1021/acs.orglett.7b02061

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