10.1002/adsc.201701188
Advanced Synthesis & Catalysis
tetrachloroethane (0.75 mL) and methanol (0.25 mL) were
added under argon. The tube was cooled to -78°C and
bis(tert-butylcarbonyloxy)iodobenzene (114 mg, 0.28
mmol, 1.4 equiv) was added. The reaction was stirred at -
35°C for 3 days. The filtrate was concentrated in vacuo and
the residue was purified by column chromatography on
silica gel using petroleum ether/ethyl acetate as eluent to
[9] a) J. W. Rigoli, C. D. Weatherly, J. M. Alderson, B. T.
Vo, J. M. Schomaker, J. Am. Chem. Soc. 2013, 135,
17238-17241; b) R. J. Scamp, J. G. Jirak, N. S. Dolan, I.
A. Guzei, J. M. Schomaker, Org. Lett. 2016, 18, 3014-
3017.
give the desired product
diastereoisomer (>99:1).
5
isolated as unique
[10] S. M. Paradine, J. R. Griffin, J. Zhao, A. L. Petronico,
S. M. Miller, M. C. White, Nat. Chem. 2015, 7, 987-994.
[11] a) N. S. Dolan, R. J. Scamp, T. Yang, J. F. Berry, J. M.
Schomaker, J. Am. Chem. Soc. 2016, 138, 14658-14667;
b) C. Liang, F. Collet, F. Robert-Peillard, P. Müller, R.
H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343-
350; c) C. Lescot, B. Darses, F. Collet, P. Retailleau, P.
Dauban, J. Org. Chem. 2012, 77, 7232-7240; d) J.
Buendia, B. Darses, P. Dauban, Angew. Chem. Int. Ed.
2015, 54, 5697-5701. For a recent comprehensive
review on allylic amination, see: e) R. L. Grangea, E. A.
Clizbeb, P. A. Evans, Synthesis 2016, 48, 2911-2968.
Acknowledgements
The authors thank the French National Research Agency (program
n° ANR-11-IDEX-0003-02, CHARMMMAT ANR-11-LABX-0039,
SynOrg ANR-11-LABX-0029, and ANR-15-CE29-0014-01) for
financial support and fellowships (G. J., R. R.-R.).
References
[1] a) H. M. L. Davies, J. R. Manning, Nature 2008, 451,
417-424; b) F. Collet, R.H. Dodd, P. Dauban, Chem.
Commun. 2009, 5061-5074 ; c) D. N. Zalatan, J. Du Bois,
Top. Curr. Chem. 2010, 292, 347-378; d) J. L. Jeffrey,
R. Sarpong, Chem. Sci. 2013, 4, 4092-4106; e) S. Chiba,
H. Chen, Org. Biomol. Chem. 2014, 12, 4051-4060 ; f)
M.-L. Louillat, F. W. Patureau, Chem. Soc. Rev. 2014,
43, 901-910; g) R. R. Karimov, A. Sharma, J. F. Hartwig,
ACS Cent. Sci. 2016, 2, 715-724; h) Y. Park, Y. Kim, S.
Chang, Chem. Rev. 2017, 117, 9247-9301.
[12] For other relevant studies in the area of chemoselective
intermolecular C(sp3)-H amination, see: a) J. L. Roizen,
D. N. Zalatan, J. Du Bois, Angew. Chem. Int. Ed. 2013,
52, 11343-11346; b) E. N. Bess, R. J. DeLuca D. J.
Tindall, M. S. Oderinde, J. L. Roizen, J. Du Bois, M. S.
Sigman, J. Am. Chem. Soc. 2014, 134, 5783-5789; c) J.
Wang, C. Zhao, Y. Weng, H. Xu, Catal. Sci. Technol.,
2016, 6, 5292-5303.
[13] a) S. Toumieux, P. Compain, O. R. Martin, M. Selkti,
Org. Lett. 2006, 8, 4493-4496; b) S. Wang, D. Romo,
Angew. Chem. Int. Ed. 2008, 47, 1284-1286; c) M. Kono,
S. Harada, T. Nemoto, Chem. Eur. J. 2017, 23, 7428-
7432.
[2] a) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905-
2960 ; b) M. M. Díaz-Requejo, P. J. Pérez, Chem. Rev.
2008, 108, 3379-3394; c) K. Huard, H. Lebel, Chem. Eur.
J. 2008, 14, 6222-6230; d) S. Fantauzzi, A. Caselli, E.
Gallo, Dalton Trans. 2009, 5434-5443; e) T. G. Driver,
Org. Biomol. Chem. 2010, 8, 3831-3846; f) J. W. W.
Chang, T. M. U. Ton, P. W. H. Chan, Chem. Rec. 2011,
11, 331-357; g) J. L. Roizen, M. E. Harvey, J. Du Bois,
Acc. Chem. Res. 2012, 45, 911-922; h) T. Uchida, T.
Katsuki, Chem. Rec. 2014, 14, 117-129; i) R. J. Scamp,
J. W. Rigoli, J. M. Schomaker, Pure Appl. Chem. 2014,
86, 381-393; j) J. Buendia, G. Grelier, P. Dauban, Adv.
Organomet. Chem. 2015, 64, 77-118.
[14] a) J. M. Howell, K. Feng, J. R. Clark, L. J. Trzepkowski,
M. C. White, J. Am. Chem. Soc. 2015, 137, 1459014593;
b) Y.-J.Liu, H. Xu, W.-J. Kong, M. Shang, H.-X. Dai,
J.-Q. Yu Nature 2014, 515, 389-393.
[15] a) S. Beaumont, V. Pons, P. Retailleau, R. H. Dodd, P.
Dauban, Angew. Chem. Int. Ed. 2010, 49, 1634-1637; b)
N. Gigant, G. Dequirez, P. Retailleau, I. Gillaizeau, P.
Dauban Chem. Eur. J. 2012, 18, 90-94; c) G. Dequirez,
J. Ciesielski, P. Retailleau, P. Dauban, Chem. Eur. J.
2014, 20, 8929-8933; d) J. Ciesielski, G. Dequirez, P.
Retailleau, V. Gandon, P. Dauban, Chem. Eur. J. 2016,
22, 9338-9347.
[3] a) D. Karila, R. H. Dodd, Curr. Org. Chem. 2011, 15,
1507-1538; b) J. Egger, E. M. Carreira, Nat. Prod. Rep.
2014, 31, 449-455; c) B. Darses, R. Rodrigues, L.
Neuville, M. Mazurais, P. Dauban, Chem. Commun.
2017, 53, 493-508.
[16] a) K. Guthikonda, J. Du Bois, J. Am. Chem. Soc. 2002,
124, 13672-13673 ; b) K. W. Fiori, J. Du Bois, J. Am.
Chem. Soc. 2007, 129, 562-568.
[4] L. Degennaro, P. Trinchera, R. Luisi, Chem. Rev. 2014,
114, 7881-7929.
[17] N. Gigant, L. Chausset-Boissarie, I. Gillaizeau, Chem.
Eur. J. 2014, 20, 7548-7564.
[5] a) D. N. Zalatan, J. Du Bois, J. Am. Chem. Soc. 2008,
130, 9220-9221 ; b) K. W. Fiori, C. G. Espino, B. H.
Brodsky, J. Du Bois, Tetrahedron 2009, 65, 3042-3051.
[18] P. Mattei, M. Boehringer, P. Di Giorgio, H. Fischer, M.
Hennig, J. Huwyler, B. Koçer, B. Kuhn, B. M. Loeffler,
A. MacDonald, R. Narquizian, Bioorg. Med. Chem.,
2010, 20, 1109-1113.
[6] M. E. Harvey, D. G. Musaev, J. Du Bois, J. Am. Chem.
Soc. 2011, 133, 17207-17216.
[19] a) 2-substituted enamides 1 were synthesized by Pd
cross-coupling reaction starting from enol phosphate
derivatives: D. Mousset, I. Gillaizeau, J. Hassan, F.
Lepifre, P. Bouyssou, G. Coudert, G. Tetrahedron Lett.
2005, 21, 3703-3705 and see Supporting Informations.
[7] S. M. Paradine, M. C. White, J. Am. Chem. Soc. 2012,
134, 2036-2039.
[8] H. Lu, H. Jiang, Y. Hu, L. Wojtas, X. P. Zhang, Chem.
Sci. 2011, 2, 2361-2366.
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