Enantioselective Automultiplication of Chiral Molecules by Asymmetric Autocatalysis

Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule

Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085

On spontaneous asymmetric synthesis

Frank, F. C. (1953) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(53)90082-1 · Cited by 905

Chemical etiology of nucleic acid structure

Eschenmoser, A. (1999) · Science · doi:10.1126/science.284.5423.2118 · Cited by 611

Circular Polarization in Star- Formation Regions: Implications for Biomolecular Homochirality

Bailey, J., Chrysostomou, A., Hough, J. H., Gledhill, T. M., McCall, A., Clark, S., Ménard, F., & Tamura, M. (1998) · Science · doi:10.1126/science.281.5377.672 · Cited by 597

Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohols. Mechanism and nonlinear effect

Kitamura, M., Okada, S., Suga, S., & Noyori, R. (1989) · Journal of the American Chemical Society · doi:10.1021/ja00193a040 · Cited by 588

Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal salts

Soai, K., Ookawa, A., Kaba, T., & Ogawa, K. (1987) · Journal of the American Chemical Society · doi:10.1021/ja00257a034 · Cited by 330

Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light

Flores, J. J., Bonner, W. A., & Massey, G. A. (1977) · Journal of the American Chemical Society · doi:10.1021/ja00453a018 · Cited by 265

Chiral N,N-dialkylnorephedrines as catalysts of the highly enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes. The asymmetric synthesis of secondary aliphatic and aromatic alcohols of high optical purity

Soai, K., Yokoyama, S., & Hayasaka, T. (1991) · The Journal of Organic Chemistry · doi:10.1021/jo00013a035 · Cited by 237

Amplification of a Slight Enantiomeric Imbalance in Molecules Based on Asymmetric Autocatalysis: The First Correlation between High Enantiomeric Enrichment in a Chiral Molecule and Circularly Polarized Light

Shibata, T., Yamamoto, J., Matsumoto, N., Yonekubo, S., Osanai, S., & Soai, K. (1998) · Journal of the American Chemical Society · doi:10.1021/ja980815w · Cited by 204

Nonlinear Effects in Asymmetric Catalysis

Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591

Asymmetric Catalysis at Chiral Metal Surfaces

Mallat, T., Orglmeister, E., & Baiker, A. (2007) · Chemical Reviews · doi:10.1021/cr0683663 · Cited by 592

Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supra-molecular polymers and assemblies

Pérez-García, L., & Amabilino, D. B. (2007) · Chem. Soc. Rev. · doi:10.1039/b610714a · Cited by 441

Chiral Autocatalysis, Spontaneous Symmetry Breaking, and Stochastic Behavior

Kondepudi, D. K., & Asakura, K. (2001) · Accounts of Chemical Research · doi:10.1021/ar010089t · Cited by 363

Catalyzed Asymmetric Arylation Reactions

Bolm, C., Hildebrand, J. P., Muñiz, K., & Hermanns, N. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20010917)40:18<3284::aid-anie3284>3.0.co;2-u · Cited by 309

Absolute Asymmetric Synthesis: A Commentary

Mislow, K. (2003) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc20030849 · Cited by 286

Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

Weissbuch, I., & Lahav, M. (2011) · Chemical Reviews · doi:10.1021/cr1002479 · Cited by 284

Asymmetric synthesis of pyrimidyl alkanol without adding chiral substances by the addition of diisopropylzinc to pyrimidine-5-carbaldehyde in conjunction with asymmetric autocatalysis

Soai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., et al. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(02)00791-7 · Cited by 266

Molecular chirality at surfaces

Ernst, K. (2012) · physica status solidi (b) · doi:10.1002/pssb.201248188 · Cited by 260

Amplification of Chirality from Extremely Low to Greater than 99.5 % ee by Asymmetric Autocatalysis

Sato, I., Urabe, H., Ishiguro, S., Shibata, T., & Soai, K. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390105 · Cited by 232

Asymmetric Autocatalysis of Pyrimidyl Alkanol and Its Application to the Study on the Origin of Homochirality

Soai, K., Kawasaki, T., & Matsumoto, A. (2014) · Accounts of Chemical Research · doi:10.1021/ar5003208 · Cited by 181

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

Barabás, B., Zucchi, C., Maioli, M., Micskei, K., & Pályi, G. (2015) · Journal of Molecular Modeling · doi:10.1007/s00894-015-2576-6 · Cited by 168

Reflections on spontaneous asymmetric synthesis by amplifying autocatalysisThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

Gridnev, I. D., Serafimov, J. M., Quiney, H., & Brown, J. M. (2003) · Organic & Biomolecular Chemistry · doi:10.1039/b307382n · Cited by 140

A Few Molecules Can Control the Enantiomeric Outcome. Evidence Supporting Absolute Asymmetric Synthesis Using the Soai Asymmetric Autocatalysis

Singleton, D. A., & Vo, L. K. (2003) · Organic Letters · doi:10.1021/ol035605p · Cited by 130

Highly enantioselective synthesis of organic compound using right- and left-handed helical silica

Sato, I., Kadowaki, K., Urabe, H., Jung, J. H., Ono, Y., Shinkai, S., & Soai, K. (2003) · Tetrahedron Letters · doi:10.1016/s0040-4039(02)02707-7 · Cited by 123

Large Nonlinear Effect Observed in the Enantiomeric Excess of Proline in Solution and That in the Solid State

Hayashi, Y., Matsuzawa, M., Yamaguchi, J., Yonehara, S., Matsumoto, Y., Shoji, M., Hashizume, D., & Koshino, H. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200601506 · Cited by 120

Enantioselective Synthesis without Discrete Optically Active Additives

Singleton, D. A., & Vo, L. K. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027129o · Cited by 118

Asymmetric Photoreactions as the Origin of Biomolecular Homochirality: A Critical Review

Jorissen, A., & Cerf, C. (2002) · Origins of life and evolution of the biosphere · doi:10.1023/a:1016087202273 · Cited by 116

Spontaneous absolute asymmetric synthesis in the presence of achiral silica gel in conjunction with asymmetric autocatalysis

Kawasaki, T., Suzuki, K., Shimizu, M., Ishikawa, K., & Soai, K. (2006) · Chirality · doi:10.1002/chir.20273 · Cited by 109

Asymmetric Synthesis Utilizing Circularly Polarized Light Mediated by the Photoequilibrium of Chiral Olefins in Conjunction with Asymmetric Autocatalysis

Sato, I., Sugie, R., Matsueda, Y., Furumura, Y., & Soai, K. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200454162 · Cited by 110

Frank Model and Spontaneous Emergence of Chirality in Closed Systems

Crusats, J., Hochberg, D., Moyano, A., & Ribó, J. M. (2009) · ChemPhysChem · doi:10.1002/cphc.200900181 · Cited by 104

Evidence 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

Welcome home, systems chemists

von Kiedrowski, G., Otto, S., & Herdewijn, P. (2010) · Journal of Systems Chemistry · doi:10.1186/1759-2208-1-1 · Cited by 102

Unraveling the Mechanism of the Soai Asymmetric Autocatalytic Reaction by First‐Principles Calculations: Induction and Amplification of Chirality by Self‐Assembly of Hexamolecular Complexes

Schiaffino, L., & Ercolani, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802450 · Cited by 100

Asymmetric Amplification Using Chiral Cocrystals Formed from Achiral Organic Molecules by Asymmetric Autocatalysis

Kawasaki, T., Jo, K., Igarashi, H., Sato, I., Nagano, M., Koshima, H., & Soai, K. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200462963 · Cited by 94

Putting the Mechanism of the Soai Reaction to the Test: DFT Study of the Role of Aldehyde and Dialkylzinc Structure

Ercolani, G., & Schiaffino, L. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102525t · Cited by 86

Quantification of Sophisticated Equilibria in the Reaction Pool and Amplifying Catalytic Cycle of the Soai Reaction

Gridnev, I. D., & Vorobiev, A. K. (2012) · ACS Catalysis · doi:10.1021/cs300497h · Cited by 84

Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality

Kawasaki, T., Shimizu, M., Nishiyama, D., Ito, M., Ozawa, H., & Soai, K. (2009) · Chemical Communications · doi:10.1039/b908754k · Cited by 83

Enantioselective synthesis induced by tetrathia-[7]-helicenes in conjunction with asymmetric autocatalysis

Kawasaki, T., Suzuki, K., Licandro, E., Bossi, A., Maiorana, S., & Soai, K. (2006) · Tetrahedron: Asymmetry · doi:10.1016/j.tetasy.2006.07.015 · Cited by 82

Evidence of asymmetric autocatalysis in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde using chiral pyrimidyl alkanol

Sato, I., Omiya, D., Tsukiyama, K., Ogi, Y., & Soai, K. (2001) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(01)00351-2 · Cited by 81

Oscillatory Symmetry Breaking in the Soai Reaction

Micskei, K., Rábai, G., Gál, E., Caglioti, L., & Pályi, G. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp803334b · Cited by 80

Asymmetric Autocatalysis: Triggered by Chiral Isotopomer Arising from Oxygen Isotope Substitution

Kawasaki, T., Okano, Y., Suzuki, E., Takano, S., Oji, S., & Soai, K. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102263 · Cited by 79

Enantioselective synthesis mediated by chiral crystal of achiral hippuric acid in conjunction with asymmetric autocatalysis

Kawasaki, T., Suzuki, K., Hatase, K., Otsuka, M., Koshima, H., & Soai, K. (2006) · Chemical Communications · doi:10.1039/b602442d · Cited by 69

Mechanistic Insights in the Reversal of Enantioselectivity of Chiral Catalysts by Achiral Catalysts in Asymmetric Autocatalysis

Lutz, F., Igarashi, T., Kinoshita, T., Asahina, M., Tsukiyama, K., Kawasaki, T., & Soai, K. (2008) · Journal of the American Chemical Society · doi:10.1021/ja077156k · Cited by 69

Molecular Chirality in Meteorites and Interstellar Ices, and the Chirality Experiment on Board the ESA Cometary Rosetta Mission

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

Chiral Symmetry Breaking in Chiral Crystallization and Soai Autocatalytic Reaction

Gridnev, I. D. (2006) · Chemistry Letters · doi:10.1246/cl.2006.148 · Cited by 68

Generation of Absolute Controlled Crystal Chirality by the Removal of Crystal Water from Achiral Crystal of Nucleobase Cytosine

Kawasaki, T., Hakoda, Y., Mineki, H., Suzuki, K., & Soai, K. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1000938 · Cited by 65

Amplification of enantiomeric excess, mirror-image symmetry breaking and kinetic proofreading in Soai reaction models with different oligomeric orders

Micheau, J.-C., Coudret, C., Cruz, J.-M., & Buhse, T. (2012) · Physical Chemistry Chemical Physics · doi:10.1039/c2cp42041d · Cited by 62

Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate

Sato, I., Kadowaki, K., Ohgo, Y., & Soai, K. (2004) · Journal of Molecular Catalysis A: Chemical · doi:10.1016/j.molcata.2004.03.010 · Cited by 58

Racemic β Sheets in Biochirogenesis

Rubinstein, I., Eliash, R., Bolbach, G., Weissbuch, I., & Lahav, M. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200605040 · Cited by 48

Spontaneous absolute asymmetric synthesis promoted by achiral amines in conjunction with asymmetric autocatalysis

Suzuki, K., Hatase, K., Nishiyama, D., Kawasaki, T., & Soai, K. (2010) · Journal of Systems Chemistry · doi:10.1186/1759-2208-1-5 · Cited by 46

Enantioselective Synthesis Induced by Compounds with Chirality Arising from Partially Deuterated Methyl Groups in Conjunction with Asymmetric Autocatalysis

Kawasaki, T., Ozawa, H., Ito, M., & Soai, K. (2011) · Chemistry Letters · doi:10.1246/cl.2011.320 · Cited by 45

Enantioselective CC Bond Formation as a Result of the Oriented Prochirality of an Achiral Aldehyde at the Single‐Crystal Face upon Treatment with a Dialkyl Zinc Vapor

Kawasaki, T., Kamimura, S., Amihara, A., Suzuki, K., & Soai, K. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102031 · Cited by 45

Asymmetric autocatalysis triggered by oxygen isotopically chiral glycerin

Matsumoto, A., Oji, S., Takano, S., Tada, K., Kawasaki, T., & Soai, K. (2013) · Organic & Biomolecular Chemistry · doi:10.1039/c3ob40293b · Cited by 45

Role of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds

Soai, K., Kawasaki, T., & Matsumoto, A. (2019) · Symmetry · doi:10.3390/sym11050694 · Cited by 44

Asymmetric autocatalysis initiated by achiral nucleic acid base adenine: implications on the origin of homochirality of biomolecules

Mineki, H., Hanasaki, T., Matsumoto, A., Kawasaki, T., & Soai, K. (2012) · Chemical Communications · doi:10.1039/c2cc34928k · Cited by 42

Discrimination of cryptochirality in chiral isotactic polystyrene by asymmetric autocatalysis

Kawasaki, T., Hohberger, C., Araki, Y., Hatase, K., Beckerle, K., Okuda, J., & Soai, K. (2009) · Chemical Communications · doi:10.1039/b912813a · Cited by 41

Determination of absolute configurations of amino acids by asymmetric autocatalysis of 2-alkynylpyrimidyl alkanol as a chiral sensor

Sato, I., Ohgo, Y., Igarashi, H., Nishiyama, D., Kawasaki, T., & Soai, K. (2007) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2006.11.042 · Cited by 38

Light on Chirality: Absolute Asymmetric Formation of Chiral Molecules Relevant in Prebiotic Evolution

Myrgorodska, I., Meinert, C., Hoffmann, S. V., Jones, N. C., Nahon, L., & Meierhenrich, U. J. (2017) · ChemPlusChem · doi:10.1002/cplu.201600214 · Cited by 40

Data-Based Stochastic Approach to Absolute Asymmetric Synthesis by Autocatalysis

Barabás, B., Caglioti, L., Micskei, K., & Pályi, G. (2009) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.82.1372 · Cited by 36

Prediction of Soai Reaction Enantioselectivity Induced by Crystals of N-(2-Thienylcarbonyl)glycine

Carter, D. J., Rohl, A. L., Shtukenberg, A., Bian, S., Hu, C., Baylon, L., Kahr, B., Mineki, H., Abe, K., Kawasaki, T., et al. (2012) · Crystal Growth & Design · doi:10.1021/cg300207d · Cited by 36

Photochirogenesis: Photochemical Models on the Origin of Biomolecular Homochirality

Meinert, C., Filippi, J.-J., Nahon, L., Hoffmann, S. V., D’Hendecourt, L., De Marcellus, P., Bredehöft, J. H., Thiemann, W. H.-P., & Meierhenrich, U. J. (2010) · Symmetry · doi:10.3390/sym2021055 · Cited by 36

On the Origin and Structure of the Recently Observed Acetal in the Soai Reaction

Gridnev, I. D., & Vorobiev, A. K. (2015) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20140341 · Cited by 35

Enantioselective Synthesis Induced by Chiral Crystal Composed of dl-Serine in Conjunction with Asymmetric Autocatalysis

Kawasaki, T., Sasagawa, T., Shiozawa, K., Uchida, M., Suzuki, K., & Soai, K. (2011) · Organic Letters · doi:10.1021/ol200616t · Cited by 34

Kinetic Insight into Specific Features of the Autocatalytic Soai Reaction

Lavabre, D., Micheau, J.-C., Islas, J. R., & Buhse, T. (2007) · Topics in Current Chemistry · doi:10.1007/128_2007_149 · Cited by 34

Enantiodivergent formation of a chiral cytosine crystal by removal of crystal water from an achiral monohydrate crystal under reduced pressure

Mineki, H., Kaimori, Y., Kawasaki, T., Matsumoto, A., & Soai, K. (2013) · Tetrahedron: Asymmetry · doi:10.1016/j.tetasy.2013.09.020 · Cited by 32

Dynamic Nonlinear Effects in Asymmetric Catalysis

Bryliakov, K. P. (2019) · ACS Catalysis · doi:10.1021/acscatal.9b00697 · Cited by 32

Enantioselective Photochromism under Circularly Polarized Light

Hashim, P. K., & Tamaoki, N. (2019) · ChemPhotoChem · doi:10.1002/cptc.201900068 · Cited by 31

Homochiral oligopeptides by chiral amplification within two-dimensional crystalline self-assemblies at the air-water interface; Relevance to biomolecular handedness

Weissbuch, I., Zepik, H., Bolbach, G., Shavit, E., Tang, M., Jensen, T. R., Kjaer, K., Leiserowitz, L., & Lahav, M. (2003) · Chemistry – A European Journal · doi:10.1002/chem.200390205 · Cited by 25

Asymmetric Autocatalysis as a Relay for Remote Amplification of Chirality of Target Molecules Used as Triggers

Funes-Maldonado, M., Sieng, B., & Amedjkouh, M. (2016) · Organic Letters · doi:10.1021/acs.orglett.6b00742 · Cited by 20

Asymmetric Synthesis with a Chiral Catalyst Generated from Asymmetric Autocatalysis

Sato, I., Urabe, H., Ishii, S., Tanji, S., & Soai, K. (2001) · Organic Letters · doi:10.1021/ol0166350 · Cited by 20

Kinetic analysis of artificial peptide self-replication. Part II: The heterochiral case

Rivera Islas, J., Pimienta, V., Micheau, J.-C., & Buhse, T. (2003) · Biophysical Chemistry · doi:10.1016/s0301-4622(02)00249-1 · Cited by 15

Physical and astrophysical aspects of the problem of origin of chiral asymmetry of the biosphere

Tsarev, V. A. (2009) · Physics of Particles and Nuclei · doi:10.1134/s1063779609070028 · Cited by 12

Isotope chirality in long‐armed multifunctional organosilicon (“Cephalopod”) molecules

Barabás, B., Kurdi, R., Zucchi, C., & Pályi, G. (2018) · Chirality · doi:10.1002/chir.22865 · Cited by 10