Donnerstag, 16. Oktober 2014, 14:15 - 15:30 iCal

"Asymmetric Autocatalysis and the Origin of Homochirality"

Prof. Kenso Soai / Tokyo University of Science

Hörsaal III der Fakultät für Chemie
Währinger Straße 38, 1090 Wien


Asymmetric Autocatalysis and the Origin of Homochirality

Kenso Soai /

Department of Applied Chemistry, Tokyo University of Science

Asymmetric autocatalysis is a reaction in which chiral product acts as chiral catalyst for its own production. The process is an automultiplic ation of a chiral compound. We

found pyrimidyl alkanol is an efficient asymmetric

autocatalysis with amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde.


Starting from pyrimidyl alkanol with extremely low

ee, three consecutive asymmetric autocatalysis enhanced

the ee to >99.5% ee with significant multiplication of the amount.

By using asymmetric autocatalysis, chiral isotopomers,


enantiotopic face of achiral crystal,


chiral inorganic mineral such as cinnabar


were found to act as the origin of chirality to afford pyrimidyl alkanols with high ee.


Asymmetric autocatalysis with large multi function

alized compound is also achieved.



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Nature, 1995,

378, 767-768.

2. T. Kawasaki, Y. Okano, E. Suzuki, S. Takano,

S. Oji, K. Soai,

Angew. Chem. Int. Ed., 2011,

50, 8131-8133.

3. T. Kawasaki, S. Kamimura, A. Amihara, K. Suzuki,

K. Soai,

Angew. Chem. Int. Ed., 2011,

50, 6796-6798.

4. H. Shindo, Y. Shirota, K. Niki, T. Kawasaki,

K. Suzuki, Y. Araki, A. Matsumoto,

K. Soai,

Angew. Chem. Int. Ed., 2013,

52, 9135-9138.

5. K. Soai, T. Kawasaki, A. Matsumoto,

Chem. Record, 2014,

14, 70-83.

6. T. Kawasaki, M. Nakaoda, Y. Takahashi, Y. Kanto,

N. Kuruhara, K. Hosoi, I. Sato,

A. Matsumoto, K. Soai,

Angew. Chem. Int. Ed., 2014.

DOI: 10.1002/anie.201405441.


Fakultät für Chemie


Brigitte Schwarz
Fakultät für Chemie der Universität Wien