Journal
ORGANIC LETTERS
Volume 18, Issue 12, Pages 2922-2925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01269
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Funding
- University of Western Ontario
- Natural Science and Engineering Research Council of Canada (NSERC)
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Tandem ring opening, elimination, and cycloaddition of donor-acceptor cyclopropanes were observed in Yb(OTf)(3)-catalyzed cycloaddition with nitrosoarenes. The reaction results in formation of tetrahydro-1,2-oxazine instead of the normal cycloadduct isoxazolidine via in situ nitrone formation. A similar cascade sequence was observed with cis-diazines. Mechanistic studies on this unique transformation offer an entirely new approach for reaction design with donor-acceptor cyclopropanes.
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