Literature DB >> 11835560

Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

Itaru Sato1, Tomotaka Yanagi, Kenso Soai.   

Abstract

2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increases the ee of pyrimidyl alkanol up to 99% without the need for any other chiral auxillary. Copyright 2002 Wiley-Liss, Inc.

Entities:  

Year:  2002        PMID: 11835560     DOI: 10.1002/chir.10068

Source DB:  PubMed          Journal:  Chirality        ISSN: 0899-0042            Impact factor:   2.437


  3 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.  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

  3 in total

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