The self-disproportionation of enantiomers (SDE): a menace or an opportunity?
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Herein we report on the well-documented, yet not widely known, phenomenon of the self-disproportionation of enantiomers (SDE): the spontaneous fractionation of scalemic material into enantioenriched and -depleted fractions when any physicochemical process is applied.
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Some mechanisms are known for increasing an existing enantiomeric excess, such as self-disproportionation of enantiomers, non-linear effects in asymmetric catalysis, and stereoselective polymerization.
“Some mechanisms are known for increasing an existing e.e., such as the self-disproportionation of enantiomers (SDE), 61 non-linear effects in asymmetric catalysis, 62,63 and stereoselective polymerization.64”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [61]
Self-disproportionation of enantiomers (SDE) is not rare for organic molecules and may occur through a wide range of physicochemical processes.
“This phenomenon of self-disproportionation of the enantiomers (SDE) is not rare for organic molecules and may occur through a wide range of physicochemical processes.61”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [61]
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Noyori, R., & Kitamura, M. (1991) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199100491 · Cited by 1,214 · see citing works
Phenomenon of Optical Self-Purification of Chiral Non-Racemic Compounds
Soloshonok, V. A., Ueki, H., Yasumoto, M., Mekala, S., Hirschi, J. S., & Singleton, D. A. (2007) · Journal of the American Chemical Society · doi:10.1021/ja065603a · Cited by 187 · see citing works
Self-citationEvidence of Asymmetric Autocatalysis in Organocatalytic Reactions
Mauksch, M., Tsogoeva, S. B., Martynova, I. M., & Wei, S. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200603517 · Cited by 103 · see citing works
Serine sublimes with spontaneous chiral amplification
Perry, R. H., Wu, C., Nefliu, M., & Cooks, R. G. (2007) · Chem. Commun. · doi:10.1039/b616196k · Cited by 97 · see citing works
An astrophysically-relevant mechanism for amino acid enantiomer enrichment
Fletcher, S. P., Jagt, R. B. C., & Feringa, B. L. (2007) · Chemical Communications · doi:10.1039/b702882b · Cited by 96 · see citing works
Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions
Mauksch, M., Tsogoeva, S. B., Wei, S., & Martynova, I. M. (2007) · Chirality · doi:10.1002/chir.20474 · Cited by 89 · see citing works
Myrgorodska, I., Meinert, C., Martins, Z., Le Sergeant d'Hendecourt, L., & Meierhenrich, U. J. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201409354 · Cited by 68 · see citing works
Flagged first, then by citations
Research works printed but not linked: 54
- (a) Martens J. Bhushan R. Helv. Chim. Acta 2014 97 161 (b) Sorochinsky A. E. and Soloshonok V. A., Self-disproportionation of Enantiomers of Enantiomerically Enriched Compounds, in Topics of Current Chemistry, Differentiation of Enantiomers II, ed. V. Schurig, Springer-Verlag GmbH, Berlin, Germany, 2013, vol. 341, pp. 301–340. 23605252
- (a) Martens J. Bhushan R. J. Liq. Chromatogr. Relat. Technol. 1992 15 1 (b) Soloshonok V. A. Roussel C. Kitagawa O. Sorochinsky A. E. Chem. Soc. Rev. 2012 41 4180 22517405 (c) Martens J. Bhushan R. Isr. J. Chem. 2016 56 990 (d) Wzorek A. Sato A. Drabowicz J. Soloshonok V. A. Isr. J. Chem. 2016 56 977 (e) Drabowicz J. Jasiak A. Wzorek A. Sato A. Soloshonok V. A. Arkivoc 2017 2017 557
- Wzorek A. Sato A. Drabowicz J. Soloshonok V. A. J. Chromatogr. A 2016 1467 270 27240946
- (a) Hirata T. Takahashi I. Suzuki Y. Yoshida H. Hasegawa H. Kitagawa O. J. Org. Chem. 2016 81 318 26646709 (b) Hirai M. Terada S. Yoshida H. Ebine K. Hirata T. Kitagawa O. Org. Lett. 2016 18 5700 27783530
- Matsuoka M. Goto M. Wzorek A. Soloshonok V. A. Kitagawa O. Org. Lett. 2017 19 2650 28459589
- Wzorek A. Sato A. Drabowicz J. Soloshonok V. A. Klika K. D. Amino Acids 2016 48 605 26704565
- Wzorek A. Klika K. D. Drabowicz J. Sato A. Aceña J. L. Soloshonok V. A. Org. Biomol. Chem. 2014 12 4738 24873904
- (a) Ogawa S. Nishimine T. Tokunaga E. Nakamura S. Shibata N. J. Fluorine Chem. 2010 131 521 (b) Sorochinsky A. E. Katagiri T. Ono T. Wzorek A. Aceña J. L. Soloshonok V. A. Chirality 2013 25 365 23716267
- Soloshonok V. A. Angew. Chem., Int. Ed. 2006 45 766 16374792
- Soloshonok V. A. Ueki H. Yasumoto M. Mekala S. Hirschi J. S. Singleton D. A. J. Am. Chem. Soc. 2007 129 12112 17850147
- Cintas P. Angew. Chem., Int. Ed. 2008 47 2918 18327866
- (a) Jacques J., Collet A. and Wilen S. H., in Enantiomers, Racemates, and Resolutions, J. Wiley & Sons, Inc., New York, Chichester, Brisbane, Toronto, 1981, p. 165. (b) Jacques J., Collet A. and Wilen S. H., in Enantiomers, Racemates, and Resolutions, J. Wiley & Sons, Inc., New York, Chichester, Brisbane, Toronto, 1981, p. 425.
- (a) Klika K. D. Budovská M. Kutschy P. J. Fluorine Chem. 2010 131 467 (b) Jung M. Schurig V. J. Chromatogr. 1992 605 161 (c) Baciocchi R. Zenoni G. Mazzotti M. Morbidelli M. J. Chromatogr. A 2002 944 225 11831757 (d) Baciocchi R. Zenoni G. Valentini M. Mazzotti M. Morbidelli M. J. Phys. Chem. A 2002 106 10461 (e) Baciocchi R. Mazzotti M. Morbidelli M. J. Chromatogr. A 2004 1024 15 14753702 (f) Gil-Av E. Schurig V. J. Chromatogr. A 1994 666 519 (g) Davankov V. A. Meyer V. R. Rais M. Chirality 1990 2 208 2083142 (h) Davankov V. A. Chromatographia 1989 27 475 (i) Kurganov A. Chromatographia 1996 43 17 (j) Schurig V. J. Chromatogr. A 2009 1216 1723 19070865 (k) Trapp O. Schurig V. Tetrahedron: Asymmetry 2010 21 1334
- Nieminen V. Murzin D. Y. Klika K. D. Org. Biomol. Chem. 2009 7 537 19156320
- Maeno M. Tokunaga E. Yamamoto T. Suzuki T. Ogino Y. Ito E. Shiro M. Asahi T. Shibata N. Chem. Sci. 2015 6 1043 29560192 PMC5811091
- Mauksch M. Tsogoeva S. B. Martynova I. M. Wei S. Angew. Chem., Int. Ed. 2007 46 393 17146824
- Mastai Y. Völkel A. Cölfen H. J. Am. Chem. Soc. 2008 130 2426 18254622
- (a) Tsuzuki S. Orita H. Ueki H. Soloshonok V. A. J. Fluorine Chem. 2010 131 461 (b) Albrecht M. Soloshonok V. A. Schrader L. Yasumoto M. Suhm M. A. J. Fluorine Chem. 2010 131 495 (c) Tonner R. Soloshonok V. A. Schwerdtfeger P. Phys. Chem. Chem. Phys. 2011 13 811 20949192 (d) Tonner R. Soloshonok V. A. Schwerdtfeger P. Phys. Chem. Chem. Phys. 2011 13 4161 20949192
- (a) Kukhar V. P. Sorochinsky A. E. Soloshonok V. A. Future Med. Chem. 2009 1 793 21426081 (b) Soloshonok V. A. Gerus I. I. Yagupolskii Y. L. Kukhar V. P. Zh. Org. Khim. 1987 23 2308
- (a) Perry R. H. Wu C. Nefliu M. Cooks R. G. Chem. Commun. 2007 1071 17325809 (b) Fletcher S. P. Jagt R. B. C. Feringa B. L. Chem. Commun. 2007 2587 17579743 (c) Bellec A. Guillemin J. C. Chem. Commun. 2010 46 1482 20162155
- Eliel E. L. and Wilen S. H., in Stereochemistry of Organic Compounds, John Wiley & Sons, 1995, pp. 179–183.
- Aceña J. L. Sorochinsky A. E. Katagiri T. Soloshonok V. A. Chem. Commun. 2013 49 373 23183684
- Cundy K. C. Crooks P. A. J. Chromatogr. 1983 281 17 6715467
- Monde K. Harada N. Takasugi M. Kutschy P. Suchý M. Dzurilla M. J. Nat. Prod. 2000 63 1312 11000049
- Suchý M. Kutschy P. Monde K. Goto H. Harada N. Takasugi M. Dzurilla M. Balentová E. J. Org. Chem. 2001 66 3940 11375018
- Terada S. Hirai M. Honzawa A. Kitagawa O. Kamizela A. Wzorek A. Soloshonok V. A. Chem.–Eur. J. 2017 23 14631 28783208
- Mayani V. J. Abdi S. H. R. Kureshy R. I. Khan N. H. Agrawal S. Jasra R. V. Chirality 2009 21 255 18561251
- Huang G. Yang J. Zhang X. Chem. Commun. 2011 47 5587 21465056
- Tur F. Saá J. M. Org. Lett. 2007 9 5079 17979280
- Netopilik M. J. Chromatogr. A 2017 1487 139 28139225
- Ishida Y. Aida T. J. Am. Chem. Soc. 2002 124 14017 12440899
- (a) Balaban T. S. Bhise A. D. Bringmann G. Bürck J. Chappaz-Gillot C. Eichhöfer A. Fenske D. Götz D. C. G. Knauer M. Mizoguchi T. Mössinger D. Rösner H. Roussel C. Schraut M. Tamiaki H. Vanthuyne N. J. Am. Chem. Soc. 2009 131 14480 19769331 (b) Higler I. Grave L. Breuning E. Verboom W. Jong F. D. Fyles T. M. Reinhoudt D. N. Eur. J. Org. Chem. 2000 1727
- (a) Ono T. Kukhar V. P. Soloshonok V. A. J. Org. Chem. 1996 61 6563 11667521 (b) Soloshonok V. A. Soloshonok I. V. Kukhar V. P. Svedas V. K. J. Org. Chem. 1998 63 1878
- Klussmann M. Mathew S. P. Iwamura H. Wells Jr D. H. Armstrong A. Blackmond D. G. Angew. Chem., Int. Ed. 2006 45 7989 17061299
- (a) Somasundaran P. Sep. Sci. 1975 10 93 (b) Somasundaran P. Sep. Purif. Methods 1972 1 117 (c) Karger B. L. DeVivo D. G. Sep. Sci. 1968 3 393
- (a) Armstrong D. W. Schneiderheinze J. M. Hwang Y.-S. Anal. Chem. 1998 70 3717 9737214 (b) Armstrong D. W. Zhou E. Y. Chen S. Le K. Tang Y. Anal. Chem. 1994 66 4278
- (a) Girard C. Kagan H. B. Angew. Chem., Int. Ed. 1998 37 2922 29711141 (b) Kagan H. B. Synlett 2001 888 (c) Guillaneux D. Zhao S. H. Samuel O. Rainford D. Kagan H. B. J. Am. Chem. Soc. 1994 116 9430 (d) Puchot C. Samuel O. Duñach E. Zhao S. Agami C. Kagan H. B. J. Am. Chem. Soc. 1986 108 2353 22175583 (e) Girard C. Kagan H. B. Can. J. Chem. 2000 78 816
- (a) Shibata T. Yamamoto J. Matsumoto N. Yonekubo S. Osanai S. Soai K. J. Am. Chem. Soc. 1998 120 12157 (b) Soai K. Kawasaki T. Chirality 2006 18 469 16676331
- Blackmond D. G. Acc. Chem. Res. 2000 33 402 10891058
- Mikami K. Terada M. Korenaga T. Matsumoto Y. Ueki M. Angelaud R. Angew. Chem., Int. Ed. 2000 39 3532 11091405
- Faller J. W. Lavoie A. R. Parr J. Chem. Rev. 2003 103 3345 12914500
- (a) Mikami K. Yamanaka M. Chem. Rev. 2003 103 3369 12914501 (b) Chen Y. Yekta S. Yudin A. K. Chem. Rev. 2003 103 3155 12914495
- (a) Diggle G. E. Int. J. Clin. Pract. 2001 55 627 11770361 (b) Miller M. T. Stromland K. K. Curr. Opin. Ophthalmol. 2011 22 356 21825994 PMC3713624
- (a) Takeuchi Y. Shiragami T. Kimura K. Suzuki E. Shibata N. Org. Lett. 1999 1 1571 (b) Yamada T. Okada T. Sakaguchi K. Ohfune Y. Ueki H. Soloshonok V. A. Org. Lett. 2006 8 5625 17107088 (c) Soloshonok V. A. Yamada T. Sakaguchi K. Ohfune Y. Future Med. Chem. 2009 1 897 21426088 (d) Osipov S. N. Tsouker P. Hennig L. Burger K. Tetrahedron 2004 60 271 (e) Man H. W. Corral L. G. Stirling D. I. Muller G. W. Bioorg. Med. Chem. Lett. 2003 13 3415 14505639
- (a) Tokunaga E. Akiyama H. Soloshonok V. A. Inoue Y. Hara H. Shibata N. PLoS One 2017 12 e0182152 28763493 PMC5538663 (b) Yamamoto T. Tokunaga E. Nakamura S. Shibata N. Toru T. Chem. Pharm. Bull. 2010 58 110 20045977 (c) Chowdhury G. Murayama N. Okada Y. Uno Y. Shimizu M. Shibata N. Guengerich F. P. Yamazaki H. Chem. Res. Toxicol. 2010 23 1018 20443640 PMC3843493 (d) Lee C. J. J. Shibata N. Wilery M. J. Wells P. G. Toxicol. Sci. 2011 122 157 21505091 (e) Yamazaki H. Suemizu H. Igaya S. Shimizu M. Shibata N. Nakamura M. Chowdhury G. Guengerich F. P. Chem. Res. Toxicol. 2011 24 287 21299192 PMC3838788
- (a) Ohishi H. In Y. Ishida T. Inque M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1989 45 1921 2635607 (b) Deng J. Chi Y. Fu F. Cui X. Yu K. Zhu J. Jiang Y. Tetrahedron: Asymmetry 2000 11 1729
- Zhang Q.-W. Xiang K. Tu Y.-Q. Zhang S.-Y. Zhang X.-M. Zhao Y.-M. Zhang T.-C. Chem.–Asian J. 2012 7 894 22383373
- (a) Maxwell R. Chickos J. J. Pharm. Sci. 2012 101 805 22081306 (b) Rietveld I. B. Barrio M. Do B. Tamarit J.-L. Céolin R. J. Phys. Chem. B 2012 116 5568 22509723
- Cintas P. Viedma C. Chirality 2012 24 894 22678980
- (a) Mauksch M. Tsogoeva S. B. Martynova I. M. Wei S. Chirality 2007 19 816 17786910 (b) Tsogoeva S. B. Wei S. Freund M. Mauksch M. Angew. Chem., Int. Ed. 2009 48 590 19072810 (c) Mauksch M. Tsogoeva S. B. ChemPhysChem 2008 9 2359 18942050
- (a) Aiba S. Takamatsu N. Sasai T. Tokunaga Y. Kawasaki T. Chem. Commun. 2016 52 10834 27492553 (b) Kawasaki T. Nakaoda M. Takahashi Y. Kanto Y. Kuruhara N. Hosoi K. Sato I. Matsumoto A. Soai K. Angew. Chem., Int. Ed. 2014 53 11199 25195925 (c) Kawasaki T. Soai K. J. Fluorine Chem. 2010 131 525
- (a) Myrgorodska I. Meinert C. Martins Z. Le Sergeant d'Hendecourt L. Meierhenrich U. J. Angew. Chem., Int. Ed. 2015 54 1402 25431250 (b) Myrgorodska I. Javelle T. Meinert C. Meierhenrich U. J. Isr. J. Chem. 2016 56 1016 (c) Pizzarello S. Cronin J. R. Nature 1998 394 236 9685155
- (a) Darquie B. Stoeffler C. Shelkovnikov A. Daussy C. Amy-Klein A. Chardonnet C. Zrig S. Guy L. Crassous J. Soulard P. Asselin P. Huet T. R. Schwerdtfeger P. Bast R. Saue T. Chirality 2010 22 870 20839292 (b) Crassous J. Chardonnet C. Saue T. Schwerdtfeger P. Org. Biomol. Chem. 2005 3 2218 16010350 (c) De Montigny F. Bast R. Severo Pereira Gomes A. Pilet G. Vanthuyne N. Roussel C. Guy L. Schwerdtfeger P. Saue T. Crassous J. Phys. Chem. Chem. Phys. 2010 12 8792 20532288
- (a) Tarasevych A. V. Sorochinsky A. E. Kukhar V. P. Guillemin J.-C. Chem. Commun. 2015 51 7054 25806861 (b) Kminek G. Bada J. L. Botta O. Glavin D. P. Grunthaner F. Planet. Space Sci. 2000 48 1087 (c) Viedma C. Ortiz J. E. de Torres T. Cintas P. Chem. Commun. 2012 48 3623 22388769 (d) Viedma C. Noorduin W. L. Ortiz J. E. de Torres T. Cintas P. Chem. Commun. 2011 47 671 21109890
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- Authors
- Han, J., Kitagawa, O., Wzorek, A., Klika, K. D., & Soloshonok, V. A.
- Affiliations
- Nanjing University (CN)
- Shibaura Institute of Technology (JP)
- Jan Kochanowski University (PL)
- German Cancer Research Center (DE)
- Ikerbasque (ES)
- Corresponding author
- Han, Jianlin
- Klika, Karel D.
- Soloshonok, Vadim A.
- Venue
- Chemical Science
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2018
- Volume
- 9
- Issue
- 7
- Pages
- 1718-1739
- ISSN
- 2041-6520 (ISSN-L)
- 2041-6539
- PMC
- PMC5892310
- OpenAlex
- W2784286141
- Cited by
- 121
- References
- 7
- Citations by year
- 2026: 8 · 2025: 7 · 2024: 11 · 2023: 20 · 2022: 14 · 2021: 20 · 2020: 13 · 2019: 18 · 2018: 10
- FWCI
- 1.92
- Type
- journal article
- Language
- en
- Open access
- diamond
- doi.org
- Licence
- Locations
- Chemical Science (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21102071, 21472082)
- Japan Society for the Promotion of Science (C 17K08220)
- Ministry of Science and Higher Education (612 561)
- Ikerbasque, Basque Foundation for Science
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Physical Sciences › Chemistry › Organic Chemistry › Chemistry and Stereochemistry Studies
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Keywords
- asymmetric catalysis, halogen bonding, hydrogen bonding, chiral selectors, racemic resolution
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