Issue 18, 2013
From the journal:

Organic & Biomolecular Chemistry

Asymmetric autocatalysis triggered by oxygen isotopically chiral glycerin†

Arimasa Matsumoto,a   Shotaro Oji,a   Shizuka Takano,a   Kyohei Tada,a   Tsuneomi Kawasakibc  and  Kenso Soai*ac  

* Corresponding authors

a Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, Japan
E-mail: soai@rs.kagu.tus.ac.jp
Fax: +81 3 5261 4631
Tel: +81 3 5228 8261

b Department of Material Science and Engineering, University of Fukui, Bunkyo, Fukui, Japan

c Research Center for Chirality, RIST, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, Japan

Abstract

Chiral (S)- and (R)-18O-glycerin induces enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, and the subsequent asymmetric autocatalysis affords (R)- and (S)-pyrimidyl alkanol with high enantiomeric excess, respectively.

Graphical abstract: Asymmetric autocatalysis triggered by oxygen isotopically chiral glycerin

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Article information

DOI
https://doi.org/10.1039/C3OB40293B
Article type
Communication
Submitted
08 Feb 2013
Accepted
05 Mar 2013
First published
05 Mar 2013

Org. Biomol. Chem., 2013,11, 2928-2931

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Asymmetric autocatalysis triggered by oxygen isotopically chiral glycerin

A. Matsumoto, S. Oji, S. Takano, K. Tada, T. Kawasaki and K. Soai, Org. Biomol. Chem., 2013, 11, 2928 DOI: 10.1039/C3OB40293B

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