4
Tetrahedron
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Scheme 3 Reaction with TEMPO as additive.
4.
Finally, the isoxazoline product 2a could be transformed to
acyclic β-hydroxyl-γ-methoxyl ketone 9 bearing two contiguous
tetrasubstituted carbons (Eq. 2).
Scheme 4 Transformation of 2a to acyclic compound.
5.
2. Conclusions
In conclusion, we have developed a PhI(OAc)2-promoted
dioxygenation of allyl oximes, including one alkoxylation. This
reaction can give isoxazoline products bearing two contiguous
tetrasubstituted carbons under mild and simple conditions.
Various oximes bearing different aryl groups and olefins were
compatible with our reaction conditions. Preliminary mechanistic
studies suggest a two-electron oxidation pathway.
6.
7.
Acknowledgments
We thank the The National Natural Science Foundation of China
(Nos. 21302124, 21620102003, 21772119), Science and
Technology Commission of Shanghai Municipality (No.
15JC1402200), and Shanghai Municipal Education Commission
(No. 201701070002E00030) for financial support.
8.
References and notes
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