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Development of Novel Hydrogen-Bond Donor Catalysts pp 51–104Cite as

Development of Hydroxy Thiourea Catalysts

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Abstract

Two novel bifunctional thioureas bearing hydroxy groups were developed. Initially, asymmetric Michael reactions of γ-hydroxyenones and organoboronic acids were examined using these catalysts. These reactions gave low yields due to the competitive, undesired oxy-Michael reaction when thiourea catalysts bearing a basic amino group were employed. In contrast, with the use of newly designed iminophenol-type catalysts, desired asymmetric Michael reactions proceed smoothly and provide vinyl addition products in high yields and ee’s. It was found that both the hydroxy groups in the substrates and the catalyst were necessary for effective catalysis in these reactions. Subsequently, the first highly catalytic, enantioselective Petasis-type reaction of N-aryl-α-iminoamides was developed using novel hydroxyether-type thioureas as catalysts. This reaction provides rapid access to unnatural vinyl glycine derivatives in high optical purity.

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  1. The Scripps Research Institute, La Jolla, 92037, CA, USA

    Tsubasa Inokuma

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Inokuma, T. (2013). Development of Hydroxy Thiourea Catalysts. In: Development of Novel Hydrogen-Bond Donor Catalysts. Springer Theses. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54231-5_3

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