10.1002/adsc.201801407
Advanced Synthesis & Catalysis
In summary, we have developed a rare olefin
Beilstein J. Org. Chem. 2013, 9, 1977; c) M. Newcomb,
J. H. Horner, H. Shahin, Tetrahedron Lett. 1993, 34,
5523; d) M. Schmittel, A. Burghart, Angew. Chem. Int.
Ed. 1997, 36, 2550.
oxyamination reaction with N-alkylanilines with
readily available reagents, that yields vicinal amino
alcohols with excellent diastereoselectivity. Therefore,
ARCs were engaged as the crucial intermediates,
which in turn were generated via a new method for the
oxidation of simple alkyl substituted anilines.
[5] a) N. Hoffmann, Synthesis 2016, 48, 1782; b) P. Kohls,
D. Jadhav, G. Pandey, O. Reiser, Org. Lett. 2012, 14,
672; c) A. McNally, C. K. Prier, D. W. C. MacMillan,
Science 2011, 334, 1114; d) Y. Miyake, K. Nakajima,
Y. Nishibayashi, J. Am. Chem. Soc. 2012, 134, 3338; e)
K. Nakajima, Y. Miyake, Y. Nishibayashi, Acc. Chem.
Res. 2016, 49, 1946; f) L. Shi, W. Xia, Chem. Soc. Rev.
2012, 41, 7687; g) D. Staveness, I. Bosque, C. R.
Stephenson, Acc. Chem. Res. 2016, 49, 2295.
Experimental Section
The alkene tethered aniline 1 (0.2 mmol, 1.0 equiv.),
TEMPO (0.3 mmol, 1.5 equiv.) and Mn(OAc)3·2H2O
(0.4 mmol, 2.0 equiv.) are dissolved in 2.0 mL THF at room
temperature and stirred for 7 h until the conversion of the
starting material is complete (monitored by TLC). For the
isolation of the product, 5 mL sat. NaHCO3-solution are
added, the aqueous phase is extracted with dichloromethane,
the combined organic phases are dried over Na2SO4, and
concentrated in vacuo. The crude product is purified by
column chromatography (pentane/ethyl acetate = 100:1).
[6] a) J. W. Beatty, C. R. Stephenson, Acc. Chem. Res. 2015,
48, 1474; b) S. A. Girard, T. Knauber, C. J. Li, Angew.
Chem. Int. Ed. 2014, 53, 74; c) M. D. Kärkäs, Chem.
Soc. Rev. 2018, 47, 5786; d) E. A. Mitchell, A.
Peschiulli, N. Lefevre, L. Meerpoel, B. U. Maes, Chem.
Eur. J. 2012, 18, 10092; e) C. K. Prier, D. A. Rankic, D.
W. MacMillan, Chem. Rev. 2013, 113, 5322; f) J.
Davies, S. G. Booth, S. Essafi, R. A. W. Dryfe, D.
Leonori, Angew. Chem. Int. Ed. 2015, 54, 14017.
Acknowledgements
We are grateful for financial support by the China Scholarship
Council (CSC).
[7] J. H. Horner, O. M. Musa, A. Bouvier, M. Newcomb, J.
Am. Chem. Soc. 1998, 120, 7738.
[8] W. R. Bowman, D. N. Clark, R. J. Marmon,
References
Tetrahedron 1994, 50, 1295.
[1] a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996,
96, 835; b) S. C. Bergmeier, Tetrahedron 2000, 56,
2561; c) J. Gante, Angew. Chem. Int. Ed. 1994, 33,
1699; d) A. Studer, Synthesis 1996, 1996, 793; e) J. B.
H. Tok, R. R. Rando, J. Am. Chem. Soc. 1998, 120,
8279.
[9] S. Maity, N. Zheng, Angew. Chem. Int. Ed. 2012, 51,
9562.
[10] A. J. Musacchio, L. Q. Nguyen, G. H. Beard, R. R.
Knowles, J. Am. Chem. Soc. 2014, 136, 12217.
[11] A. J. Musacchio, B. C. Lainhart, X. Zhang, S. G.
Naguib, T. C. Sherwood, R. R. Knowles, Science 2017,
355, 727.
[2] a) J. A. Bodkin, M. D. McLeod, J. Chem. Soc., Perkin
Trans. 1 2002, 2733; b) T. J. Donohoe, C. K. Callens,
A. Flores, A. R. Lacy, A. H. Rathi, Chem. Eur. J. 2011,
17, 58; c) X.-W. Lan, N.-X. Wang, Y. Xing, Eur. J. Org.
Chem. 2017, 2017, 5821; d) K. Muniz, Chem. Soc. Rev.
2004, 33, 166; e) D. Nilov, O. Reiser, Adv. Synth. Catal.
2002, 344, 1169; f) X. Ren, Q. Guo, J. Chen, H. Xie, Q.
Xu, Z. Lu, Chem. Eur. J. 2016, 22, 18695.
[12] a) A. L. Bartelson, K. M. Lambert, J. M. Bobbitt, W. F.
Bailey, ChemCatChem 2016, 8, 3421; b) R. Ciriminna,
M. Pagliaro, Org. Process Res. Dev. 2010, 14, 245; c)
A. Gini, T. Brandhofer, O. G. Mancheño, Org. Biomol.
Chem. 2017, 15, 1294; d) J. E. Nutting, M. Rafiee, S. S.
Stahl, Chem. Rev. 2018, 118, 4834; e) B. L. Ryland, S.
S. Stahl, Angew. Chem. Int. Ed. 2014, 53, 8824; f) L.
Tebben, A. Studer, Angew. Chem. Int. Ed. 2011, 50,
5034.
[3] a) J. R. Chen, X. Q. Hu, L. Q. Lu, W. J. Xiao, Chem.
Soc. Rev. 2016, 45, 2044; b) M. D. Kärkäs, ACS
Catalysis 2017, 7, 4999; c) M. Minozzi, D. Nanni, P.
Spagnolo, Chem. Eur. J. 2009, 15, 7830; d) S. A. Morris,
J. Wang, N. Zheng, Acc. Chem. Res. 2016, 49, 1957; e)
R. S. Neale, Synthesis 1971, 1971, 1; f) L. Stella, Angew.
Chem. Int. Ed. 1983, 22, 337; g) T. Xiong, Q. Zhang,
Chem. Soc. Rev. 2016, 45, 3069; h) S. Z. Zard, Chem.
Soc. Rev. 2008, 37, 1603; i) X.-Q. Hu, J.-R. Chen, Q.
Wei, F.-L. Liu, Q.-H. Deng, A. M. Beauchemin, W.-J.
Xiao, Angew. Chem. Int. Ed. 2014, 53, 12163; j) Y.
Zhao, W. Xia, Chem. Soc. Rev. 2018, 47, 2591; k) X. Q.
Hu, J. Chen, J. R. Chen, D. M. Yan, W. J. Xiao, Chem.
Eur. J. 2016, 22, 14141; l) X. Deng, K. Liang, X. Tong,
M. Ding, D. Li, C. Xia, Org. Lett. 2014, 16, 3276.
[13] a) X. Y. Duan, X. L. Yang, R. Fang, X. X. Peng, W.
Yu, B. Han, J. Org. Chem. 2013, 78, 10692; b) X. Y.
Duan, N. N. Zhou, R. Fang, X. L. Yang, W. Yu, B. Han,
Angew. Chem. Int. Ed. 2014, 53, 3158.
[14] CCDC 1869702 contains the supplementary crystallo-
graphic data for 2d. These data can be obtained free of
charge from The Cambridge Crystallographic Data
[15] I. Colomer, R. C. Barcelos, K. E. Christensen, T. J.
Donohoe, Org. Lett. 2016, 18, 5880.
[16] E. G. Bagryanskaya, S. R. Marque, Chem. Rev. 2014,
114, 5011.
[4] a) J. H. Horner, F. N. Martinez, O. M. Musa, M.
Newcomb, H. E. Shahin, J. Am. Chem. Soc. 1995, 117,
11124; b) J. Hu, J. Wang, T. H. Nguyen, N. Zheng,
[17] J. L. Liu, Z. F. Zhu, F. Liu, Org. Lett. 2018, 20, 720.
4
This article is protected by copyright. All rights reserved.