10.1002/anie.202007595
Angewandte Chemie International Edition
RESEARCH ARTICLE
Lett. 2010, 39, 643–645.
Acknowledgements
[20]
[21]
[22]
[23]
[24]
S. D. Vaidya, S. T. Toenjes, N. Yamamoto, S. M. Maddox,
J. L. Gustafson, J. Am. Chem. Soc. 2020, 142, 2198–2203.
M. S. Betson, J. Clayden, C. P. Worrall, S. Peace, Angew.
Chem. Int. Ed. Engl. 2006, 45, 5803–5807.
J. Clayden, C. P. Worrall, W. J. Moran, M. Helliwell, Angew.
Chemie Int. Ed. 2008, 47, 3234–3237.
We thank Prof. Craig Butts and Dr. Stefano Crespi for helpful
discussions. The work was funded by the University of Bristol, the
EPSRC Centre for Doctoral Training in Synthesis for Biology and
Medicine (EP/L015838/1), supported by AstraZeneca, Diamond
Light Source, Defence Science and Technology Laboratory,
Evotec, GlaxoSmithKline, Janssen, Novartis, Pfizer, Syngenta,
Takeda, UCB and Vertex, and an Oxford-Radcliffe Scholarship,
and it used the Cirrus UK National Tier-2 HPC Service at EPCC
and EPSRC (EP/P020267/1).
J. Clayden, J. Senior, M. Helliwell, Angew. Chemie Int. Ed.
2009, 48, 6270–6273.
T. Mino, Y. Tanaka, Y. Hattori, T. Yabusaki, H. Saotome,
M. Sakamoto, T. Fujita, J. Org. Chem. 2006, 71, 7346–
7353.
[25]
[26]
J. Clayden, S. P. Fletcher, J. Senior, C. P. Worrall,
Tetrahedron: Asymmetry 2010, 21, 1355–1360.
A. Lodola, S. Bertolini, M. Biagetti, S. Capacchi, F.
Facchinetti, P. M. Gallo, A. Pappani, M. Mor, D. Pala, S.
Rivara, F. Visentini, M. Corsi, A. M. Capelli, J. Med. Chem.
2017, 60, 4304–4315.
Keywords: diarylamine • atropisomer • free energy surface •
molecular dynamics • dynamic stereochemistry
[1]
[2]
[3]
D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev.
2014, 114, 9047–9153.
S. Sakane, J. Fujiwara, K. Maruoka, H. Yamamoto, J. Am.
Chem. Soc. 1983, 105, 6154–6155.
[27]
[28]
S. R. Laplante, P. J. Edwards, L. D. Fader, A. Jakalian, O.
Hucke, ChemMedChem 2011, 6, 505–513.
A. J. Fugard, A. S. K. Lahdenperä, J. S. J. Tan, A.
Mekareeya, R. S. Paton, M. D. Smith, Angew. Chemie Int.
Ed. 2019, 58, 2795–2798.
T. D. James, K. R. A. Samankumara Sandanayake, S.
Shinkai, Nature 1995, 374, 345–347.
[4]
[5]
J. Clayden, Angew. Chemie Int. Ed. 1997, 36, 949–951.
E. Kumarasamy, R. Raghunathan, M. P. Sibi, J. Sivaguru,
Chem. Rev. 2015, 115, 11239–11300.
[29]
[30]
J. Clayden, Chem. Commun. 2004, 4, 127–135.
S. M. Raders, J. N. Moore, J. K. Parks, A. D. Miller, T. M.
Leißing, S. P. Kelley, R. D. Rogers, K. H. Shaughnessy, J.
Org. Chem. 2013, 78, 4649–4664.
[6]
[7]
[8]
[9]
S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K.
A. Jørgensen, Chem. - A Eur. J. 2006, 12, 6039–6052.
S. T. Toenjes, J. L. Gustafson, Future Med. Chem. 2018,
10, 409–422.
[31]
CCDC 1842707 and 1842708 contain the supplementary
crystallographic data for compounds 6c and 6s
respectively. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
J. Clayden, W. J. Moran, P. J. Edwards, S. R. Laplante,
Angew. Chemie - Int. Ed. 2009, 48, 6398–6401.
G. Bringmann, S. Tasler, H. Endress, K. Messer, M.
Wohlfarth, W. Lobin, D.- Wu, J. Am. Chem. Soc. 2001, 123,
2703–2712.
[32]
K. C. Gross, P. G. Seybold, Int. J. Quantum Chem. 2000,
80, 1107–1115.
[10]
G. Bringmann, T. Gulder, M. Reichert, F. Meyer, Org. Lett.
2006, 8, 1037–1040.
[33]
[34]
[35]
O. Trapp, Anal. Chem. 2006, 78, 189–198.
M. Ōki, in Top. Stereochem., 1983, pp. 1–81.
A. Laio, M. Parrinello, Proc. Natl. Acad. Sci. 2002, 99,
12562–12566.
[11]
[12]
A. A. Kanakis, V. Sarli, Org. Lett. 2010, 12, 4872–4875.
D. P. Curran, G. R. Hale, S. J. Geib, A. Balog, Q. B. Cass,
A. L. G. Degani, M. Z. Hernandes, L. C. G. Freitas,
Tetrahedron: Asymmetry 1997, 8, 3955–3975.
J. Clayden, H. Turner, M. Helliwell, E. Moir, J. Org. Chem.
2008, 73, 4415–4423.
[36]
Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215–
241.
[13]
[14]
[37]
[38]
C. Riplinger, F. Neese, J. Chem. Phys. 2013, 138, 034106.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem.
B 2009, 113, 6378–6396.
R. Costil, H. J. A. Dale, N. Fey, G. Whitcombe, J. V.
Matlock, J. Clayden, Angew. Chemie - Int. Ed. 2017, 56,
12533–12537.
[39]
Similar mechanistic features were modelled at a much
lower level of theory for the analogous ethers: see ref 21.
M. Charton, J. Am. Chem. Soc. 1975, 97, 1552–1556.
M. Charton, J. Org. Chem. 1976, 41, 2217–2220.
B. J. Price, J. A. Eggleston, I. O. Sutherland, J. Chem. Soc.
B Phys. Org. 1966, 88, 922–925.
[15]
[16]
[17]
[18]
[19]
Y. Iwasaki, R. Morisawa, S. Yokojima, H. Hasegawa, C.
Roussel, N. Vanthuyne, E. Caytan, O. Kitagawa, Chem. - A
Eur. J. 2018, 24, 4453–4458.
[40]
[41]
[42]
G. Furukawa, T. Shirai, Y. Homma, E. Caytan, N.
Vanthuyne, D. Farran, C. Roussel, O. Kitagawa, J. Org.
Chem. 2020, 85, 5109–5113.
[43]
[44]
Y. Suzuki, M. Kageyama, R. Morisawa, Y. Dobashi, H.
Hasegawa, S. Yokojima, O. Kitagawa, Chem. Commun.
2015, 51, 11229–11232.
T. Kawabata, C. Jiang, K. Hayashi, K. Tsubaki, T.
Yoshimura, S. Majumdar, T. Sasamori, N. Tokitoh, J. Am.
Chem. Soc. 2009, 131, 54–55.
J. Sangster, J. Phys. Chem. Ref. Data 1989, 18, 1111–
1229.
K. Hayashi, N. Matubayasi, C. Jiang, T. Yoshimura, S.
Majumdar, T. Sasamori, N. Tokitoh, T. Kawabata, J. Org.
Chem. 2010, 75, 5031–5036.
K. Hayashi, Y. Nakajima, F. Ozawa, T. Kawabata, Chem.
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