Literature DB >> 14601994

A few molecules can control the enantiomeric outcome. Evidence supporting absolute asymmetric synthesis using the Soai asymmetric autocatalysis.

Daniel A Singleton1, Loan K Vo.   

Abstract

[reaction: see text] Experiments were carried out to investigate whether the Soai asymmetric autocatalysis can accomplish true absolute asymmetric synthesis. In 54 reactions, R and S enantiomeric products were obtained 27 times each. Of 25 pairs of side-by-side identical reactions, 12 afforded opposite enantiomers. In a test of the mechanistic viability of a random-chance process, it was found that a very few molecules (approximately 60 000) were sufficient to control the enantiomeric outcome of these reactions. These observations appear most consistent with asymmetric synthesis originating from the chance enantiomeric excess in a racemate.

Mesh:

Year:  2003        PMID: 14601994     DOI: 10.1021/ol035605p

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Asymmetric autocatalysis and its implications for the origin of homochirality.

Authors:  Donna G Blackmond
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

2.  Isotope chirality and asymmetric autocatalysis: a possible entry to biological chirality.

Authors:  Béla Barabás; Luciano Caglioti; Károly Micskei; Claudia Zucchi; Gyula Pályi
Journal:  Orig Life Evol Biosph       Date:  2008-06-03       Impact factor: 1.950

Review 3.  Spontaneous mirror symmetry breaking and origin of biological homochirality.

Authors:  Josep M Ribó; David Hochberg; Joaquim Crusats; Zoubir El-Hachemi; Albert Moyano
Journal:  J R Soc Interface       Date:  2017-12       Impact factor: 4.118

4.  Mirror-symmetry breaking in the Soai reaction: a kinetic understanding.

Authors:  Jesús Rivera Islas; Dominique Lavabre; Jean-Michel Grevy; Ramón Hernández Lamoneda; Haydée Rojas Cabrera; Jean-Claude Micheau; Thomas Buhse
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-20       Impact factor: 11.205

Review 5.  Asymmetric Autocatalysis as an Efficient Link Between the Origin of Homochirality and Highly Enantioenriched Compounds.

Authors:  Kenso Soai; Tsuneomi Kawasaki; Arimasa Matsumoto
Journal:  Orig Life Evol Biosph       Date:  2022-08-12       Impact factor: 1.120

6.  Structural Contributions to Autocatalysis and Asymmetric Amplification in the Soai Reaction.

Authors:  Soumitra V Athavale; Adam Simon; K N Houk; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2020-10-14       Impact factor: 15.419

7.  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.

Authors:  Tsuneomi Kawasaki; Sayaka Kamimura; Ai Amihara; Kenta Suzuki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-15       Impact factor: 15.336

8.  Emergence of single-molecular chirality from achiral reactants.

Authors:  René R E Steendam; Jorge M M Verkade; Tim J B van Benthem; Hugo Meekes; Willem J P van Enckevort; Jan Raap; Floris P J T Rutjes; Elias Vlieg
Journal:  Nat Commun       Date:  2014-11-21       Impact factor: 14.919

Review 9.  Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules.

Authors:  Kenso Soai
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2019       Impact factor: 3.493

10.  Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess.

Authors:  Arimasa Matsumoto; Takaaki Abe; Atsushi Hara; Takayuki Tobita; Taisuke Sasagawa; Tsuneomi Kawasaki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-23       Impact factor: 15.336

  10 in total

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