21 Asymmetric Synthesis Involving Dynamic Enantioselective …
455
31. Boyle Jr., W.J., Sifniades, S., Van Peppen, J.F.: Asymmetric transformation of α-amino-εcaprolactam, a lysine precursor. J. Org. Chem. 44, 4841–4847 (1979)
32. Noorduin, W.L., Bode, A.A.C., van der Meijden, M., Meekes, H., van Etteger, A.F., van Enckevort, W.J.P., Christianen, P.C.M., Kaptein, B., Kellogg, R.M., Rasing, T., Vlieg, E.: Complete
chiral symmetry breaking of an amino acid derivative directed by circularly polarized light.
Nat. Chem. 1, 729–732 (2009)
33. Noorduin, W.L., Izumi, T., Millemaggi, A., Leeman, M., Meekes, H., van Enckevort, W.J.P.,
Kellogg, R.M., Kaptein, B., Vlieg, E., Blackmond, D.G.: Emergence of a single solid chiral
state from a nearly racemic amino acid derivative. J. Am. Chem. Soc. 130, 1158–1159 (2008)
34. Leeman, M., Noorduin, W.L., Millemaggi, A., Vlieg, E., Meekes, H., van Enckevort, W.J.P.,
Kaptein, B., Kellogg, R.M.: Efficient Havinga-Kondepudi resolution of conglomerate amino
acid derivatives by slow cooling and abrasive grinding. Cryst. Eng. Comm. 12, 2051–2053
(2010)
35. Obara, Y., Matsumoto, H., Arai, K., Tsuchiya, S.: Optical resolution of N-(substituted
phenylmethylidene)phenylalanine methyl esters. Jpn. Kokai Tokkyo Koho, 1986, JP6100165
(1986)
36. Hein, J.E., Huynh, C.B., Viedma, C., Kellogg, R.M., Blackmond, D.G.: Pasteur’s tweezers
revisited: on the mechanism of attrition-enhanced deracemization and resolution of chiral
conglomerate solids. J. Am. Chem. Soc. 134, 12629–12636 (2012)
37. Tsogoeva, S.B., Wei, S., Freund, M., Mauksch, M.: Generation of highly enantioenriched crystalline products in reversible asymmetric reactions with racemic or achiral catalysts. Angew.
Chem. Int. Ed. 48, 590–594 (2009)
38. Spix, L., Meekes, H., Blaauw, R.H., van Enckevort, W.J.P., Vlieg, E.E.: Complete deracemization of proteinogenic glutamic acid using Viedma ripening on a metastable conglomerate.
Cryst. Growth Des. 12, 5796–5799 (2012)
39. Lopez, F.J., Ferrino, S.A., Reyes, M.S., Roman, R.: Asymmetric transformation of the second
kind of racemic naproxen. Tetrahedron. Asymm. 8, 2497–2500 (1977)
40. Noorduin, W.L., Kaptein, B., Meekes, H., van Enckevort, W.J.P., Kellogg, R.M., Vlieg, E.: Fast
attrition-enhanced deracemization of naproxen by a gradual in situ feed. Angew. Chem. Int.
Ed. 48, 4581–4583 (2009)
41. Hachiya, S., Kasashima, Y., Yagishita, F., Mino, T., Masu, H., Sakamoto, M.: Asymmetric
transformation by dynamic crystallization of achiral succinimides. Chem. Commun. 49, 4776–
4778 (2013)
42. Engwerda, A.H.J., Mertens, J.C.J., Tinnemans, P., Meekes, H., Rutjes, F.P.J.T., Vlieg, E.: Solidphase conversion of four stereoisomers into a single enantiomer. Angew. Chem. Int. Ed. 57,
15441–15444 (2018)
43. Yagishita, F., Ishikawa, H., Onuki, T., Hachiya, S., Mino, T., Sakamoto, M.: Total spontaneous resolution by deracemization of isoindolinones. Angew. Chem. Int. Ed. 51, 13023–13025
(2012)
44. Sakamoto, M., Shiratsuki, K., Uemura, N., Ishikawa, H., Yoshida, Y., Kasashima, Y., Mino,
T.: Asymmetric synthesis by using natural sunlight under absolute achiral conditions. Chem.
Eur. J. 23, 1717–1721 (2017)
45. Ishikawa, H., Uemura, N., Saito, R., Yoshida, Y., Mino, T., Kasashima, Y., Sakamoto, M.:
Chiral symmetry breaking of spiropyrans and spirooxazines by dynamic enantioselective
crystallization. Chem. Eur. J. 25, 9758–9763 (2019)
46. Engwerda, A.H.J., Koning, N., Tinnemans, P., Meekes, H., Bickelhaupt, F.M., Rutjes, F.P.J.T.,
Vlieg, E.: Deracemization of a racemic allylic sulfoxide using Viedma ripening. Cryst. Growth
Des. 17, 4454–4457 (2017)
47. Pincock, R.E., Perkins, R.R., Ma, A.S., Wilson, K.R.: Probability distribution of enantiomorphous forms in spontaneous generation of optically active substances. Science 174, 1018–1020
(1971)
48. Kondepudi, D.K., Laudadio, J., Asakura, K.: Chiral symmetry breaking in stirred crystallization
of 1,1 -binaphthyl melt. J. Am. Chem. Soc. 121, 1448–1451 (1999)
455
31. Boyle Jr., W.J., Sifniades, S., Van Peppen, J.F.: Asymmetric transformation of α-amino-εcaprolactam, a lysine precursor. J. Org. Chem. 44, 4841–4847 (1979)
32. Noorduin, W.L., Bode, A.A.C., van der Meijden, M., Meekes, H., van Etteger, A.F., van Enckevort, W.J.P., Christianen, P.C.M., Kaptein, B., Kellogg, R.M., Rasing, T., Vlieg, E.: Complete
chiral symmetry breaking of an amino acid derivative directed by circularly polarized light.
Nat. Chem. 1, 729–732 (2009)
33. Noorduin, W.L., Izumi, T., Millemaggi, A., Leeman, M., Meekes, H., van Enckevort, W.J.P.,
Kellogg, R.M., Kaptein, B., Vlieg, E., Blackmond, D.G.: Emergence of a single solid chiral
state from a nearly racemic amino acid derivative. J. Am. Chem. Soc. 130, 1158–1159 (2008)
34. Leeman, M., Noorduin, W.L., Millemaggi, A., Vlieg, E., Meekes, H., van Enckevort, W.J.P.,
Kaptein, B., Kellogg, R.M.: Efficient Havinga-Kondepudi resolution of conglomerate amino
acid derivatives by slow cooling and abrasive grinding. Cryst. Eng. Comm. 12, 2051–2053
(2010)
35. Obara, Y., Matsumoto, H., Arai, K., Tsuchiya, S.: Optical resolution of N-(substituted
phenylmethylidene)phenylalanine methyl esters. Jpn. Kokai Tokkyo Koho, 1986, JP6100165
(1986)
36. Hein, J.E., Huynh, C.B., Viedma, C., Kellogg, R.M., Blackmond, D.G.: Pasteur’s tweezers
revisited: on the mechanism of attrition-enhanced deracemization and resolution of chiral
conglomerate solids. J. Am. Chem. Soc. 134, 12629–12636 (2012)
37. Tsogoeva, S.B., Wei, S., Freund, M., Mauksch, M.: Generation of highly enantioenriched crystalline products in reversible asymmetric reactions with racemic or achiral catalysts. Angew.
Chem. Int. Ed. 48, 590–594 (2009)
38. Spix, L., Meekes, H., Blaauw, R.H., van Enckevort, W.J.P., Vlieg, E.E.: Complete deracemization of proteinogenic glutamic acid using Viedma ripening on a metastable conglomerate.
Cryst. Growth Des. 12, 5796–5799 (2012)
39. Lopez, F.J., Ferrino, S.A., Reyes, M.S., Roman, R.: Asymmetric transformation of the second
kind of racemic naproxen. Tetrahedron. Asymm. 8, 2497–2500 (1977)
40. Noorduin, W.L., Kaptein, B., Meekes, H., van Enckevort, W.J.P., Kellogg, R.M., Vlieg, E.: Fast
attrition-enhanced deracemization of naproxen by a gradual in situ feed. Angew. Chem. Int.
Ed. 48, 4581–4583 (2009)
41. Hachiya, S., Kasashima, Y., Yagishita, F., Mino, T., Masu, H., Sakamoto, M.: Asymmetric
transformation by dynamic crystallization of achiral succinimides. Chem. Commun. 49, 4776–
4778 (2013)
42. Engwerda, A.H.J., Mertens, J.C.J., Tinnemans, P., Meekes, H., Rutjes, F.P.J.T., Vlieg, E.: Solidphase conversion of four stereoisomers into a single enantiomer. Angew. Chem. Int. Ed. 57,
15441–15444 (2018)
43. Yagishita, F., Ishikawa, H., Onuki, T., Hachiya, S., Mino, T., Sakamoto, M.: Total spontaneous resolution by deracemization of isoindolinones. Angew. Chem. Int. Ed. 51, 13023–13025
(2012)
44. Sakamoto, M., Shiratsuki, K., Uemura, N., Ishikawa, H., Yoshida, Y., Kasashima, Y., Mino,
T.: Asymmetric synthesis by using natural sunlight under absolute achiral conditions. Chem.
Eur. J. 23, 1717–1721 (2017)
45. Ishikawa, H., Uemura, N., Saito, R., Yoshida, Y., Mino, T., Kasashima, Y., Sakamoto, M.:
Chiral symmetry breaking of spiropyrans and spirooxazines by dynamic enantioselective
crystallization. Chem. Eur. J. 25, 9758–9763 (2019)
46. Engwerda, A.H.J., Koning, N., Tinnemans, P., Meekes, H., Bickelhaupt, F.M., Rutjes, F.P.J.T.,
Vlieg, E.: Deracemization of a racemic allylic sulfoxide using Viedma ripening. Cryst. Growth
Des. 17, 4454–4457 (2017)
47. Pincock, R.E., Perkins, R.R., Ma, A.S., Wilson, K.R.: Probability distribution of enantiomorphous forms in spontaneous generation of optically active substances. Science 174, 1018–1020
(1971)
48. Kondepudi, D.K., Laudadio, J., Asakura, K.: Chiral symmetry breaking in stirred crystallization
of 1,1 -binaphthyl melt. J. Am. Chem. Soc. 121, 1448–1451 (1999)