Oxidative Kinetic Resolution of cis-Fused Tricyclic 1-Tetralone Derivatives by Guanidine–Bisurea Bifunctional Organocatalyst

Minami Odagi; Keisuke Hosoya; Yoshiharu Yamamoto; Kazuo Nagasawa

doi:10.1055/s-0036-1588151

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(11): 1305-1309
DOI: 10.1055/s-0036-1588151

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Oxidative Kinetic Resolution of cis-Fused Tricyclic 1-Tetralone Derivatives by Guanidine–Bisurea Bifunctional Organocatalyst

Minami Odagi*

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588, Tokyo, Japan eMail: odagi@cc.tuat.ac.jp eMail: knaga@cc.tuat.ac.jp

,

Keisuke Hosoya

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588, Tokyo, Japan eMail: odagi@cc.tuat.ac.jp eMail: knaga@cc.tuat.ac.jp

,

Yoshiharu Yamamoto

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588, Tokyo, Japan eMail: odagi@cc.tuat.ac.jp eMail: knaga@cc.tuat.ac.jp

,

Kazuo Nagasawa*

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588, Tokyo, Japan eMail: odagi@cc.tuat.ac.jp eMail: knaga@cc.tuat.ac.jp

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Abstract

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Abstract

We present an enantioselective synthesis of cis-fused tricyclic 1-tetralones via oxidative kinetic resolution in the presence of cumene hydroperoxide (CHP) and guanidine–bisurea bifunctional organocatalyst. This reaction affords the corresponding α-hydroxylation products together with unreacted tetralones in good to high enantioselectivity, with s values as high as 42. The reaction was successfully applied for the synthesis of the core structure of a kainoid derivative, 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid (MFPA).

Key words

tetralone - oxidative kinetic resolution - guanidine - urea

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References and Notes
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