Literature DB >> 29711547

Practically Perfect Asymmetric Autocatalysis with (2-Alkynyl-5-pyrimidyl)alkanols.

Takanori Shibata1, Shigeru Yonekubo1, Kenso Soai1.   

Abstract

Extremely high enantioselectivity (>99.5% ee) and chemical yield (>99%) are achieved in an asymmetric autocatalytic reaction. A (5-pyrimidyl)alkanol with a tert-butylethynyl group at its 2-position (1) is a very efficient asymmetric autocatalyst in the enantioselective alkylation in Equation (1). © 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Aldehydes; Alkylations; Asymmetric synthesis; Autocatalysis; Zinc

Year:  1999        PMID： 29711547     DOI： 10.1002/(SICI)1521-3773(19990301)38:5<659::AID-ANIE659>3.0.CO;2-P

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

Review 2.  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

3.  On the origins of life's homochirality: Inducing enantiomeric excess with spin-polarized electrons.

Authors:  S Furkan Ozturk; Dimitar D Sasselov
Journal:  Proc Natl Acad Sci U S A       Date:  2022-07-05       Impact factor: 12.779

4.  Discrimination of cryptochirality in chiral isotactic polystyrene by asymmetric autocatalysis.

Authors:  Tsuneomi Kawasaki; Christiane Hohberger; Yuko Araki; Kunihiko Hatase; Klaus Beckerle; Jun Okuda; Kenso Soai
Journal:  Chem Commun (Camb)       Date:  2009-08-21       Impact factor: 6.222

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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