10.1002/adsc.201900660
Advanced Synthesis & Catalysis
Acknowledgements
[9] a) M. Uyanik, T. Mutsuga, K. Ishihara, Angew.
Chem., Int. Ed. 2017, 56, 3956; b) R. Coffinier, M. El
Assal, P. A. Peixoto, C. Bosset, K. Miqueu, J.-M.
Sotiropoulos, L. Pouysegu, S. Quideau, Org. Lett. 2016,
18, 1120; c) C. Bosset, R. Coffinier, P. A. Peixoto, M.
El Assal, K. Miqueu, J. M. Sotiropoulos, L. Pouysegu,
S. Quideau, Angew. Chem., Int. Ed. 2014, 53, 9860; d)
J. K. Boppisetti, V. B. Birman, Org. Lett. 2009, 11,
1221; e) S. Quideau, G. Lyvinec, M. Marguerit, K.
Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D.
Cavagnat, A. Chenede, Angew. Chem., Int. Ed. 2009,
48, 4605; f) N. Lebrasseur, J. Gagnepain, A. Ozanne-
Beaudenon, J. M. Leger, S. Quideau, J. Org. Chem.
2007, 72, 6280; g) J. Gagnepain, F. Castet, S. Quideau,
Angew. Chem. Int. Ed. 2007, 46, 1533.
The authors thank Ministerio de Economía y Competitividad
(Grant CTQ2017-83309-P) for financial support.
References
[1] a) S. Quideau, L. Pouysegu, P. A. Peixoto, D.
Deffieux, Top. Curr. Chem. 2016, 373, 25; b) S. P.
Roche, J. A. Porco, Jr., Angew. Chem., Int. Ed. 2011,
50, 4068; c) L. Pouysegu, D. Deffieux, S. Quideau,
Tetrahedron 2010, 66, 2235; d) S. Quideau, L.
Pouysegu, D. Deffieux, Synlett 2008, 467; e) D.
Magdziak, S. J. Meek, T. R. R. Pettus, Chem. Rev.
2004, 104, 1383.
[10] S. A. Baker Dockrey, A. L. Lukowski, M. R. Becker,
[2] a) A. Flores, E. Cots, J. Berges, K. Muñiz, Adv. Synth.
Catal. 2019, 361, 2; b) W. Sun, G. Li, L. Hong, R.
Wang, Org. Biomol. Chem. 2016, 14, 2164; c) W.-T.
Wu, L. Zhang, S.-L. You, Chem. Soc. Rev., 2016, 45,
1570; d) M. Uyanik, K. Ishihara, “Asymmetric
Oxidative Dearomatization Reaction”, ed. by You, S.-L.
John Wiley & Sons, 2016, pp. 129-152; e) A. M.
Harned, Tetrahedron Lett. 2014, 55, 4681; f) Q. Ding,
Y. Ye, R. Fan, Synthesis 2013, 45, 1; (g) C.-X. Zhuo,
W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51,
12662.
A. R. H. Narayan, Nature Chem. 2018, 10, 119.
[11] a) M. C. Carreño, M. González-López, A. Urbano,
Angew. Chem., Int. Ed. 2006, 45, 2737; b) S. Barradas,
M. C. Carreño, M. González-López, A. Latorre, A.
Urbano, Org. Lett. 2007, 9, 5019; c) S. Barradas, A.
Urbano, M. C. Carreño, Chem. Eur. J. 2009, 15, 9286;
d) S. Barradas, G. Hernández-Torres, A. Urbano, M. C.
Carreño, Org. Lett. 2012, 14, 5952; e) S. Vila-Gisbert,
A. Urbano, M. C. Carreño, Chem. Commun. 2013, 49,
3561; f) M. J. Cabrera-Afonso, S. R. Lucena, Á.
Juarranz, A. Urbano, M. C. Carreño, Org. Lett. 2018,
20, 6094.
[3] a) L. Pouysegu, M. Marguerit, J. Gagnepain, G.
Lyvinec, A. J. Eatherton, S. Quideau, Org. Lett. 2008,
10, 5211; b) J. O. Omolo, H. Anke, S. Chhabra, O. J.
Sterner, Nat. Prod. 2000, 63, 975.
[12] H. Hussain, I. R. Green, I. Ahmed, Chem. Rev. 2013,
113, 3329.
[13] a) A. Saeed, F. A. Larik, B. Lal, M. Faisal, H. El-
Seedi, P. A. Channar, Synth. Commun. 2017, 47, 835;
b) L. D’Accolti, C. Annese, C. Fusco, Curr. Org. Chem.
2015, 19, 45; c) V. P. Srivastava, Synlett. 2008, 626.
[4] a) A. Sib, T. A. M. Gulder, Angew. Chem., Int. Ed.
2018, 57, 14650; b) A. M. Harned, K. A. Volp, Nat.
Prod. Rep. 2011, 28, 1790; c) L. H. Pettus, R. W. Van
de Water, T. R. R. Pettus, Org. Lett. 2001, 3, 905; d) J.
L. Wood, B. D. Thompson, N. Yusuff, D. A. Pflum, M.
S. P. Matthaeus, J. Am. Chem. Soc. 2001, 123, 2097; e)
S. Sperry, G. J. Samuels, P. Crews, J. Org. Chem. 1998,
63, 10011.
[14] a) M. K. Wong, Y. C. Yip, D. Yang, Top. Organomet.
Chem. 2011, 36, 123; b) Y. Shi, Acc. Chem. Res. 2004,
37, 488; c) M. Frohn, Y. Shi, Synthesis 2000, 1979; d)
S. E. Denmark, Z. Wu, Synlett 1999, 847.
[5] a) M. Bergner, D. C. Duquette, L. Chio, B. M. Stoltz,
Org. Lett. 2015, 17, 3008; b) M. J. Palframan, G.
Kociok-Koehn, S. E. Lewis, Org. Lett. 2011, 13, 3150;
c) Y.-H. Liao, L.-Z. Xu, S.-H. Yang, J. Dai, Y.-S. Zhen,
M. Zhu, N.-J. Sun, Phytochem. 1997, 45, 729.
[15] a) W. Adam, A. Schonberger, Tetrahedron Lett. 1992,
33, 53; b) A. Altamura, C. Fusco, L. D'Accolti, R.
Mello, T. Prencipe, R. Curci, Tetrahedron Lett. 1991,
32, 5445; c) K. Crandall, M. Zueco, R. S. Kirsch, D. M.
Coppert, Tetrahedron Lett. 1991, 32, 5441.
[6] Recent work: a) J. Dhineshkumar, P. Samaddar, K. R.
Prabhu, Chem. Commun. 2016, 52, 11084; b) S. Dong,
J. Zhu, J. A. Porco, Jr., J. Am. Chem. Soc. 2008, 130,
2738; c) J. Zhu, N. P. Grigoriadis, J. P. Lee, J. A. Porco,
Jr., J. Am. Chem. Soc. 2005, 127, 9342; Early work: d)
K. Krohn, G. Zimmermann, J. Org. Chem. 1998, 63,
4140.
[16] The fast addition of Oxone (in one portion) to a
solution of NaHCO3 in acetone/water generates a
mixture of DMDO and singlet oxygen: a) A. Lange, H.-
D. Brauer, J. Chem. Soc., Perkin Trans. 2, 1999, 805;
b) L. Cassidei, M. Fiorentino, R. Mello, O. Sciacovelli,
R. Curci, J. Org. Chem. 1987, 52, 699.
[17] N. Hashimoto, A. Kanda, Org Proc. Res. Dev. 2002,
6, 405.
[7] Recent work: a) D. Sarkar, M. K. Ghosh, N. Rout, S.
Giri, RSC Adv. 2016, 6, 26886; Early work: b) D. H. R.
Barton, S. V. Ley, P. D. Magnus, M. N. Rosenfeld, J.
Chem. Soc., Perkin Trans. 1 1977, 567.
[18] The reaction of 1a with a catalytic hypervalent iodine
reagent generated in situ, using MCPBA as co-oxidant,
gave 5a in 9% yield, together with a 16% of 3a and a
21% of unreacted 1a: see ref. 9e.
[8] a) Y. Zhang, Y. Liao, X. Liu, X. Xu, L. Lin, X. Feng,
Chem. Sci. 2017, 8, 6645; b) C. Grandclaudon, P. Y.
Toullec, Eur. J. Org. Chem. 2016, 260.
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