Diastereoselective photodimerization reactions of chromone-2-carboxamides to construct a C2-chiral scaffold

Fumitoshi Yagishita; Nozomi Baba; Yuki Ueda; Satoshi Katabira; Yoshio Kasashima; Takashi Mino; Masami Sakamoto

doi:10.1039/C4OB01827C

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Diastereoselective photodimerization reactions of chromone-2-carboxamides to construct a C₂-chiral scaffold†

Fumitoshi Yagishita,^a Nozomi Baba,^a Yuki Ueda,^a Satoshi Katabira,^a Yoshio Kasashima,^b Takashi Mino^a and Masami Sakamoto*^a

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* Corresponding authors

^a Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi, Inage, Chiba 263-8522, Japan
E-mail: sakamotom@faculty.chiba-u.jp

^b Education Center, Chiba Institute of Technology, Shibazono 2-2-1, Narashino, Chiba 275-0023, Japan

Abstract

Irradiation of three chromone-2-carboxamides with a chiral auxiliary resulted in diastereoselective formation of a C₂-chiral anti-HH dimer scaffold. Selection of the solvent polarity and decreasing the temperature resulted in asymmetric induction with up to 84% diastereomeric excess (de).

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Article information

DOI: https://doi.org/10.1039/C4OB01827C
Article type: Paper
Submitted: 27 Aug 2014
Accepted: 02 Oct 2014
First published: 02 Oct 2014

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Org. Biomol. Chem., 2014,12, 9644-9649

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Diastereoselective photodimerization reactions of chromone-2-carboxamides to construct a C₂-chiral scaffold

F. Yagishita, N. Baba, Y. Ueda, S. Katabira, Y. Kasashima, T. Mino and M. Sakamoto, Org. Biomol. Chem., 2014, 12, 9644 DOI: 10.1039/C4OB01827C

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Organic & Biomolecular Chemistry