Organic Letters
Letter
Scheme 3. Proposed Reaction Mechanism
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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I.D.J. acknowledges the Fulbright Foundation for a Junior
Faculty Award and the support of Fapesp (2015/20809-4).
H.M.L.D. was supported by the National Science Foundation
(CHE 1465189). Instrumentation used in this work was
supported by the National Science Foundation (CHE 1531620
and CHE 1626172). We thank Dr. John Bacsa (Emory
University, U.S.) for the X-ray structure determination of 3a.
Scheme 4. Scope of the Metal-Free One-Pot Protocol for the
Insertion of Aryl Diazoacataes into N−O Bonds of Isoxazol-5-
ones
REFERENCES
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(1) (a) Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc.
2011, 133, 6449−6457. (b) Wang, H.; Glorius, F. Angew. Chem., Int. Ed.
2012, 51, 7318−7322. (c) Rakshit, S.; Grohmann, C.; Besset, T.;
Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350−2353. (d) Hyster, T. K.;
Rovis, T. Synlett 2013, 24, 1842−1844. (e) Wodrich, M. D.; Ye, B.;
Gonthier, J. F.; Corminboeuf, C.; Cramer, N. Chem. - Eur. J. 2014, 20,
15409−15418. (f) Zhang, H.; Wang, K.; Wang, B.; Yi, H.; Hu, F.; Li, C.;
Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 13234−13238.
(g) Li, B.; Ma, J.; Wang, N.; Feng, H.; Xu, S.; Wang, B. Org. Lett. 2012,
14, 736−739. (h) Presset, M.; Oehlrich, D.; Rombouts, F.; Molander, G.
A. Org. Lett. 2013, 15, 1528−1531. (i) Webb, N. J.; Marsden, S. P.; Raw,
S. A. Org. Lett. 2014, 16, 4718−4721. (j) Wu, J.-Q.; Zhang, S.-S.; Gao,
H.; Qi, Z.; Zhou, C.-J.; Ji, W.-W.; Liu, Y.; Chen, Y.; Li, Q.; Li, X.; Wang,
H. J. Am. Chem. Soc. 2017, 139, 3537−3545. (k) Wu, S.; Zeng, R.; Fu, C.;
Yu, Y.; Zhang, X.; Ma, S. Chem. Sci. 2015, 6, 2275−2285.
(2) Benkovics, T.; Guzei, I. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2010,
49, 9153−9157.
(3) (a) Miyata, O.; Takeda, N.; Morikami, Y.; Naito, T. Org. Biomol.
Chem. 2003, 1, 254−256. (b) Takeda, N.; Miyata, O.; Naito, T. Eur. J.
Org. Chem. 2007, 2007, 1491−1509.
(4) (a) Manning, J. R.; Davies, H. M. L. Tetrahedron 2008, 64, 6901−
6908. (b) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130,
8602−8603.
(5) (a) Capreti, N. M. R.; Jurberg, I. D. Org. Lett. 2015, 17, 2490−2493.
(b) Jurberg, I. D. Chem. - Eur. J. 2017, 23, 9716−9720.
(6) Selected references: (a) Davies, H. M. L.; Beckwith, R. E. J. Chem.
Rev. 2003, 103, 2861−2903. (b) Davies, H. M. L.; Manning, J. R. Nature
2008, 451, 417−424. (c) Davies, H. M. L.; Morton, D. Chem. Soc. Rev.
2011, 40, 1857−1869. (d) Liao, K.; Negretti, S.; Musaev, D. G.; Bacsa, J.;
Davies, H. M. L. Nature 2016, 533, 230−234.
(7) (a) Fu, P.; La, S.; MacMillan, J. B. J. Nat. Prod. 2016, 79, 455−462.
(b) Kim, M. C.; Lee, J. H.; Shin, B.; Subedi, L.; Cha, J. W.; Park, J.-S.; Oh,
D.-C.; Kim, S. Y.; Kwon, H. C. Org. Lett. 2015, 17, 5024−5027.
(8) Hu, Y.; Potts, M. B.; Colosimo, D.; Herrera-Herrera, M. L.; Legako,
A. G.; Yousufuddin, M.; White, M. A.; MacMillan, J. B. J. Am. Chem. Soc.
2013, 135, 13387−13392.
(9) CCDC 1563347 contains supplementary crystallographic data for
this paper. These data can be obtained free of charge from the
(10) The elimination proposed in 4 is a reasonable event in light of the
following references: (a) Attanasi, O. A.; Bartoccini, S.; Favi, G.; Giorgi,
G.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2012, 68, 608−613.
(b) Beccalli, E. M.; Marchesini, A.; Gelmi, M. L.; Pilati, T. J. Org. Chem.
1987, 52, 1666−1669.
catalyzed carbene reactions, especially in transformations that
lead to the formation of nonchiral products. The protocols
introduced in this work contribute to the advancement of the
synthesis of 1,3-oxazin-6-ones 3, thus potentially allowing a wider
access to these molecules and their application in medicine and
related fields.
ASSOCIATED CONTENT
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* Supporting Information
The Supporting Information is available free of charge on the
Experimental procedures and NMR data for all new
Crystallographic data for compound 3a (CIF)
C
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