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54:
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Kawasaki T, Tanaka H, Tsutsumi T, Kasahara T, Sato I, Soai K (May 2006). "Chiral discrimination of cryptochiral saturated quaternary and tertiary hydrocarbons by asymmetric autocatalysis".
110:)-bis(dimethylamino)butane, whose chirality results solely due to the difference between N and N (7% isotopic mass difference), gave 45% ee when used as a stoichiometric ligand.
256:
Shibata T, Morioka H, Hayase T, Choji K, Soai K (1996). "Highly
Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol".
138:
36:
of the product. The product pyrimidyl alcohol is chiral and induces that same chirality in further catalytic cycles. Starting with a low
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Soai K, Shibata T, Morioka H, Choji K (1995). "Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule".
75:, with the major product of that first reaction being rapidly amplified. For example, Soai's group has demonstrated that even chiral
64:(1950–) discovered the reaction in 1995. For his work in "elucidating the origins of chirality and homochirality", Soai received the
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40:("ee") produces a product with very high enantiomeric excess. The reaction has been studied for clues about the origin of
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Micskei K, Rábai G, Gál E, Caglioti L, Pályi G (July 2008). "Oscillatory symmetry breaking in the Soai reaction".
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The chiral induction is believed to occur as a result of interactions between the C–H bonds of the alkane and the
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site for binding the nucleophile, are nonetheless capable of inducing asymmetric catalysis in the reaction.
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344:"Asymmetric Induction by a Nitrogen N/ N Isotopomer in Conjunction with Asymmetric Autocatalysis"
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Islas JR, Lavabre D, Grevy JM, Lamoneda RH, Cabrera HR, Micheau JC, Buhse T (September 2005).
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Matsumoto A, Ozaki H, Harada S, Tada K, Ayugase T, Ozawa H, et al. (December 2016).
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Caglioti L, Hajdu C, Holczknecht O, Zékány L, Zucchi C, Micskei K, Pályi G (June 2006).
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Chirality and Life: A Short
Introduction to the Early Phases of Chemical Evolution
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Proceedings of the
National Academy of Sciences of the United States of America
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Proceedings of the
National Academy of Sciences of the United States of America
156:"Asymmetric autocatalysis and its implications for the origin of homochirality"
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Other chiral additives can be used as the initial source of
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In another example, Soai and coworkers showed that even (
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and leads to rapidly increasing amounts of the same
507:"New aspects of Soai's asymmetric autocatalysis"
480:"The concept of racemates and the Soai reaction"
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309:Journal of the American Chemical Society
258:Journal of the American Chemical Society
505:Podlech J, Gehring T (September 2005).
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451:The Journal of Physical Chemistry B
284:"CSJ Award 2010: Prof. Kenso Soai"
79:hydrocarbons, which have no clear
24:of pyrimidine-5-carbaldehyde with
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286:. The Chemical Society of Japan
127:FlĂĽgel RM (January 11, 2011).
1:
133:. Springer. pp. 16–17.
154:Blackmond DG (April 2004).
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16:In organic chemistry, the
66:Chemical Society of Japan
44:among certain classes of
493:: 62–80. Archived from
423:10.1073/pnas.0503171102
181:10.1073/pnas.0308363101
524:10.1002/anie.200501742
360:10.1002/anie.201608955
60:The Japanese chemist
73:asymmetric induction
414:2005PNAS..10213743I
354:(49): 15246–15249.
227:1995Natur.378..767S
172:2004PNAS..101.5732B
38:enantiomeric excess
500:on 12 August 2017.
28:. The reaction is
561:Organic reactions
511:Angewandte Chemie
463:10.1021/jp803334b
348:Angewandte Chemie
321:10.1021/ja061429e
270:10.1021/ja953066g
221:(6559): 767–768.
140:978-3-642-16977-9
99:of the aldehyde.
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97:pi electrons
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46:biomolecules
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81:Lewis basic
545:Categories
290:2015-04-14
114:References
77:quaternary
62:KensĹŤ Soai
34:enantiomer
22:alkylation
556:Catalysis
487:Viva Orig
533:16078286
471:18593153
442:16174731
378:27754589
329:16669661
200:15067112
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410:Bibcode
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223:Bibcode
168:Bibcode
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