Nazarov Cyclization and Tandem [4 + 2]-Cycloaddition
Reactions of Donor–Acceptor Cyclopropanes
Posted on 2017-08-17 - 21:08
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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Sudhakar, Gangarajula; Mahesh, S. K.; Vemulapalli, S. Phani Babu; Nanubolu, Jagadeesh Babu (2017). Nazarov Cyclization and Tandem [4 + 2]-Cycloaddition
Reactions of Donor–Acceptor Cyclopropanes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02061
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AUTHORS (4)
GS
Gangarajula Sudhakar
SM
S. K. Mahesh
SV
S. Phani Babu Vemulapalli
JN
Jagadeesh Babu Nanubolu