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Synthesis 2010(23): 3999-4006  
DOI: 10.1055/s-0030-1258268
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Control of 1,2- Versus 1,4-Addition in Organocatalytic Reactions of o-Hydroxycinnamaldehydes with Organoboronic Acids

Kwang-Su Choi, Sung-Gon Kim*
Department of Chemistry, College of Natural Science, Kyonggi University, San 94-6, Iui-dong, Yeongtong-gu, Suwon, 443-760, Republic of Korea
Fax: +82(31)2499631; e-Mail: sgkim123@kgu.ac.kr;
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Publication History

Received 2 August 2010
Publication Date:
22 September 2010 (online)

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Abstract

The regioselective 1,2-addition and 1,4-addition reactions of o-hydroxycinnamaldehydes with organoboronic acids in the presence of organocatalysts gave 2-substituted 2H-chromenes and 4-substituted chroman-2-ols, respectively. Diethylamine was used as the catalyst for the 1,4-addition reaction, whereas dibenzyl­amine and trichloroacetic acid were used as the catalyst and additive, respectively, in the 1,2-addition reaction.

Key words

catalysis - addition reactions - heterocycles - regioselectivity - chromanols - chromenes

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