Organic Letters
Letter
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oxygen atom, which is ideal for hydrogen abstraction.
Therefore, cationic intermediate D was formed from C after
elimination of phenylhydroxylamine radical and could react
with another equivalent of indole to form intermediate E.
Deprotonation of E led to the final product 6, along with the
detectable phenylhydroxylamine by GC−MS analysis.
In summary, we have discovered an efficient and mild
method to access isoxazolidine via visible-light-mediated
cycloaddition which is antiregioselective to the typical 1,3-
dipolar nitrone cycloaddition reactions. The reaction is
highlighted by its synthetically useful yields and low catalyst
loading without other additives. Meanwhile the bis(indole)-
methanes can also be obtained in this protocol by simply
changing to indole substrates, which demonstrate the potential
application of this method in organic synthesis.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures and spectral data for all
X-ray data for compound 4a (CIF)
X-ray data for compound 4d (CIF)
(10) CCDC 1491708 (4a) and 1491709 (4d) contain the
supplementary crystallographic data for this paper. These data can
be obtained free of charge from the Cambridge Crystallographic Data
Information for X-ray data for 4a and 4d).
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AUTHOR INFORMATION
Corresponding Authors
■
ORCID
Notes
The authors declare no competing financial interest.
(12) (a) Pindur, U.; Lemster, T. Curr. Med. Chem. 2001, 8, 1681.
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Lett. 2008, 269, 326. (d) Kochanowska-Karamyan, A. J.; Hamann, M.
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ACKNOWLEDGMENTS
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We are grateful for the financial supports from China NSFC
(Nos. 21372055, 21472030, 21672047, and 21302029),
SKLUWRE (No. 2017DX03), and the Fundamental Research
Funds for the Central Universities (Grant No. HIT.BRE-
TIV.201310).
(13) Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
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