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A Dual Arylboronic Acid-Aminothiourea Catalytic System for the Asymmetric Intramolecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids

Takumi Azuma, Akihiro Murata, Yusuke Kobayashi, Tsubasa Inokuma and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

T. Azuma, A. Murata, Y. Kobayashi, T. Inokuma, Y. Takemoto, Org. Lett., 2014, 16, 4256-4259.

DOI: 10.1021/ol501954r  (free Supporting Information)


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Abstract

A bifunctional aminoboronic acid facilitates intramolecular aza- and oxa-Michael reactions of α,β-unsaturated carboxylic acids. The combination of an arylboronic acid with a chiral aminothiourea enables enantioselective conversions to afford the desired heterocycles in high yields and ee's (up to 96% ee).

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Key Words

2,3-dihydrobenzofurans, chromans


ID: J54-Y2014