Stereoselective aldol reactions using pseudo C2 symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

Yuta Inoue; Takahiro Hatayama; Tomoko Kawasaki-Takasuka; Tomohiro Agou; Toshio Kubota; Takashi Yamazaki

doi:10.1039/C8CC05458D

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Stereoselective aldol reactions using pseudo C₂ symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione†

Yuta Inoue,^a Takahiro Hatayama,^a Tomoko Kawasaki-Takasuka,^a Tomohiro Agou,

^b Toshio Kubota

^b and Takashi Yamazaki

*^a

Author affiliations

* Corresponding authors

^a Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan
E-mail: tyamazak@cc.tuat.ac.jp

^b Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan

Abstract

Crossed aldol reactions of the CF₃-containing pseudo C₂ symmetric cyclic imide 3 were carried out by way of the corresponding boron bisenolate to stereoselectively furnish the desired products 4 and this procedure allowed the preferential construction of the diastereomers of the compounds previously obtained from the acyclic counterpart 1.

This article is part of the themed collection: Fluorine Chemistry

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Article information

DOI: https://doi.org/10.1039/C8CC05458D
Article type: Communication
Submitted: 06 jul. 2018
Accepted: 06 ago. 2018
First published: 06 ago. 2018

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Chem. Commun., 2018,54, 9913-9916

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Stereoselective aldol reactions using pseudo C₂ symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

Y. Inoue, T. Hatayama, T. Kawasaki-Takasuka, T. Agou, T. Kubota and T. Yamazaki, Chem. Commun., 2018, 54, 9913 DOI: 10.1039/C8CC05458D

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