Literature DB >> 21761523

Asymmetric autocatalysis: triggered by chiral isotopomer arising from oxygen isotope substitution.

Tsuneomi Kawasaki1, Yasushi Okano, Etsuharu Suzuki, Shizuka Takano, Shotaro Oji, Kenso Soai.   

Abstract

Trigger happy: chiral oxygen isotopomers of hydrobenzoin ([(18)O](R)-1 and [(18)O](S)-1) acted as chiral triggers to induce the enantioselective addition of iPr(2)Zn to pyrimidine-5-carbaldehyde. An extremely small chiral influence arising from the presence of the oxygen isotope ((18)O) is amplified through asymmetric autocatalysis to enantioenrich the 5-pyrimidyl alkanol product.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21761523     DOI： 10.1002/anie.201102263

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  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

2.  Rationalization of Asymmetric Amplification via Autocatalysis Triggered by Isotopically Chiral Molecules.

Authors:  Neil A Hawbaker; Donna G Blackmond
Journal:  ACS Cent Sci       Date:  2018-06-06       Impact factor: 14.553

Review 3.  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

4.  Unidirectional Rotary Motion in Isotopically Chiral Molecular Motors: A Computational Analysis.

Authors:  Jun Wang; Baswanth Oruganti; Bo Durbeej
Journal:  Org Lett       Date:  2020-08-21       Impact factor: 6.005

5.  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

6.  Asymmetric Induction by a Nitrogen 14 N/15 N Isotopomer in Conjunction with Asymmetric Autocatalysis.

Authors:  Arimasa Matsumoto; Hanae Ozaki; Shunya Harada; Kyohei Tada; Tomohiro Ayugase; Hitomi Ozawa; Tsuneomi Kawasaki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-18       Impact factor: 15.336
  6 in total

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