10.1002/anie.201916480
Angewandte Chemie International Edition
RESEARCH ARTICLE
[18] S. Qu, M. Greenhalgh, A. D. Smith, Chem. Eur. J. 2019, 25, 1064-
1075. For other examples of enantioselective acylation processes
developed within our group see
Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G.
A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino,
B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz,
A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F.
Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D.
Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang,
M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida,
T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell,
J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J.
Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R.
Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant,
S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo,
R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J.
B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
[32] a) J. Chai, M. Head-Gordon, J. Chem. Phys. 2008, 10, 6615–6620;
b) A. N. Bootsma, S. Wheeler, ChemRxiv 2019. Gaussian 16,
Revision A.03, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E.
Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G.
A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J.
Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J.
V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding,
F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson,
D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W.
Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M.
Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K.
Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J.
Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov,
T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P.
Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam,
M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K.
Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc.,
Wallingford CT, 2016.
[19] Desymmetrization of
a limited number of biaryl diesters using
enzymatic deacylation has been reported For example see: a) T.
Matsumoto, T. Konegawa, T. Nakamura, K. Suzuki, Synlett, 2002,
0122–0124; b) S. Yamaguchi, N. Takahashi, D. Yuyama, K.
Sakamoto, K. Suzuki, T. Matsumoto, Synlett 2016, 27, 1262–1268;
c) M. Ochiai, Y. Akisawa, D. Kajiyama, T. Matsumoto, Synlett 2019,
30, 557–562.
[20] S. Lu, S. B. Poh, Z Rong, Y. Zhao, Org. Lett. 2019, 21, 6169–6172.
[21] J. Merad, J. Pons, O. Chuzel, C. Bressy, Eur. J. Org. Chem. 2016,
5589–5610.
[22] A. S. Burns, A. J. Wagner, J. L. Fulton, A. Zakarian, S. D. Rychnovsky,
Org. Lett. 2017, 19, 2953–2956.
[23] a) V. B. Birman, X. Li, Org. Lett. 2006, 8, 1351–1354; b) X. Li, H.
Jiang, E. W. Uffman, L. Guo, Y. Zhang, X. Yang, V. B. Birman, J. Org.
Chem. 2012, 77, 1722–1737; c) Q. Hu, H. Zhou, X. Geng, P. Chen,
Tetrahedron 2009, 65, 2232–2238; d) P. Chen, Y. Zhang, H. Zhou,
Q. Xu, Acta Chim. Sinica 2010, 68, 1431; e) I. Shiina, K. Nakata, K.
Ono, M. Sugimoto, A. Sekiguchi, Chem. Eur. J. 2010, 16, 167–172;
f) I. Shiina, K. Ono, K. Nakata, Chem. Lett. 2011, 40, 147–149; g) K.
Nakata, K. Gotoh, K. Ono, K. Futami, I. Shiina, Org. Lett. 2013, 15,
1170–172; h) I. Shiina, K. Ono, T. Nakahara, Chem. Commun. 2013,
49, 10700–10702; i) D. Belmessieri, C. Joannesse, P. A. Woods, C.
MacGregor, C. Jones, C. D. Campbell, C. P. Johnson, N. Duguet, C.
Concellón, R. A. Bragg, A. D. Smith, Org. Biomol. Chem. 2011, 9,
559–570; j) S. F. Musolino, O. S. Ojo, N. J. Westwood, J. E. Taylor,
A. D. Smith, Chem. Eur. J. 2016, 22, 18916–18922; k) S. Harrer, M.
D. Greenhalgh, R. M. Neyappadath, A. D. Smith, Synlett, 2019, 30,
1555–1560.
[24] M. D. Greenhalgh, S. M. Smith, D. M. Walden, J. E. Taylor, Z. Brice,
E. R. T. Robinson, C. Fallan, D. B. Cordes, A. M. Z. Slawin, H. C.
Richardson, M. A. Groves, P. H.-Y. Cheong, A. D. Smith, Angew.
Chem. Int. Ed. 2018, 57, 3200–3206.
[33] For a comprehensive review see M. Nishio, Phys. Chem. Chem. Phys.
2011, 13, 13873–13900.
[34] For useful reviews and accounts see a) For a review on nitrogen
cation-p interactions in organocatalysis see: S. Yamada, J. S. Fossey,
Org. Biomol. Chem. 2011, 9, 7275–7281; b) C. R. Kennedy, S. Lin,
E. N. Jacobsen, Angew. Chem. Int. Ed. 2016, 55, 12596–12624; c)
D. A. Dougherty, Acc. Chem. Res. 2013, 46, 885–893; d) S. Yamada,
Chem. Rev. 2018, 118, 11353-11432. For selected applications in
isothiourea mediated catalysis see e) T. H. West, D. M. Walden, J. E.
Taylor, A. C. Brueckner, R. C. Johnston, P. H.-Y. Cheong, G. C.
Lloyd-Jones, A. D. Smith, J. Am. Chem. Soc. 2017, 139, 4366–4375;
f) S. S. M. Spoehrle, T. H. West, J. E. Taylor, A. M. Z. Slawin, A. D.
Smith, J. Am. Chem. Soc. 2017, 139, 11895–11902; g) K. Kasten, A.
M. Z. Slawin, A. D. Smith, Org. Lett. 2017, 19, 5182–5185.
[25] a) V. B. Birman, H. Jiang, X. Li, Org. Lett. 2007, 9, 3237–3240; b) J.
Merad, P. Borkar, T. B. Yenda, C. Roux, J.-M. Pons, J.-L. Parrain, O.
Chuzel, C. Bressy, Org. Lett. 2015, 17, 2118–2121; c) J. Merad, P.
Borkar, F. Caijo, J.-M. Pons, J.-L. Parrain, O. Chuzel, C. Bressy,
Angew. Chem. Int. Ed. 2017, 56, 16052–10656; For a review of the
acylative desymmetrization of meso-diols, see: d) Á. Enríquez-García,
E. P. Kündig, Chem. Soc. Rev. 2012, 41, 7803–7831.
[26] a) J. P. Vigneron, M. Dhaenens, A. Horeau, Tetrahedron 1973, 29,
1055–1059; b) W. Kroutil, A. Kleewein, K. Faber, Tetrahedron:
Asymmetry, 1997, 8, 3251–3261;
[27] CCDC 1952952 (6) contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre.
[35] For an interesting review see C. R. Martinez, B. L. Iverson, Chem.
Sci. 2012, 3, 2191–2201.
[28] a) M. D. Greenhalgh, J. E. Taylor, A. D. Smith, Tetrahedron, 2018,
74, 5554-5560; For derivation of s see: b) H. B. Kagan, J. C. Fiaud,
Top. Stereochem. 1988, 18, 249–330.
[36] For selected overviews see a) J. Neel, M. J. Hilton, M. S. Sigman, F.
D. Toste, Nature, 2017, 543, 637–646; b) R. R. Knowles, E. N.
Jacobsen and D. W. C. Macmillan, Proc. Nat. Acad. Sci. 2010, 107,
20678–20685.
[29] Selectivity factor (s) is the most commonly used metric to report the
efficiency of a KR, and is defined as the rate constant for the fast
reacting enantiomer divided by the rate constant for the slow reacting
enantiomer (s = kfast/kslow). See references [26a] and [26b] for more
details. Based on our previous work and estimations of error in
enantioselective acylation reactions s is given to the closest integer
in this manuscript.
[37] Non-covalent S···O interactions have recognized importance in
medicinal chemistry: a) B. R. Beno, K.-S. Yeung, M. D. Bartberger, L.
D. Pennington, N. A. Meanwell, J. Med. Chem., 2015, 58, 4383–
4438; b) X. Zhang, Z. Gong, J. Li, T. Lu, J. Chem. Inf. Model. 2015,
55, 2138–2153; For selected discussions of S···O interactions in
isothiourea-catalyzed reactions, see reference 22c and c) V. B.
Birman, X. Li, Z. Han, Org. Lett. 2007, 9, 37–40; d) P. Liu, X. Yang,
V. B. Birman, K. N. Houk, Org. Lett. 2012, 14, 3288–3291; e) E. R. T.
Robinson, D. M. Walden, C. Fallan, M. D. Greenhalgh, P. H.-Y.
Cheong, A. D. Smith, Chem. Sci. 2016, 7, 6919–6927;For an
excellent discussion on the origin of chalcogen-bonding interactions
see: f) D. J. Pascoe, K. B. Ling, S. L. Cockcroft, J. Am. Chem. Soc.
2017, 139, 15160–15167.
[30] J. C. Ianni, Computational Fluid and Solid Mechanics, 2003, K. J.
Bathe, Ed., Elsevier Science Ltd: Oxford, pp. 1368–1372
[31] a) Y. Zhao, D. G. Truhlar, Theor Chem Account 2008, 120, 215–241;
b) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys., 1972, 56,
2257–2261; c) J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev., 2005,
105, 2999–3093; d) J. R. Cheeseman, G. W. Trucks, T. A. Keith and
J. Frisch, J. Chem. Phys. 1996, 104, 5497–5509; Gaussian 09,
Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E.
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