Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4500-4503Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02061
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Funding
- Science and Engineering Research Board (SERB), DST, New Delhi, India [EMR/2016/002289]
- UGC, New Delhi, India
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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.
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