Issue 20, 2020
From the journal:

Chemical Communications

Construction of trifluoromethylated quaternary stereocenters via p-quinone methides†

Kyu Terashima,a   Tomoko Kawasaki-Takasuka, ORCID logo a   Tomohiro Agou, ORCID logo b   Toshio Kubota ORCID logo b  and  Takashi Yamazaki ORCID logo *a  

* 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

Development of a new synthetic method for the construction of quaternary centers with a trifluoromethyl group was realized by way of 1,6-addition of various nucleophiles including active methylene compounds to highly reactive δ-trifluoromethylated p-quinone methides generated in situ from the corresponding tertiary carbonates with a catalytic amount of an appropriate base.

Graphical abstract: Construction of trifluoromethylated quaternary stereocenters via p-quinone methides

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Article information

DOI
https://doi.org/10.1039/C9CC08936E
Article type
Communication
Submitted
15 Nov 2019
Accepted
03 Feb 2020
First published
04 Feb 2020

Chem. Commun., 2020,56, 3031-3034

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Construction of trifluoromethylated quaternary stereocenters via p-quinone methides

K. Terashima, T. Kawasaki-Takasuka, T. Agou, T. Kubota and T. Yamazaki, Chem. Commun., 2020, 56, 3031 DOI: 10.1039/C9CC08936E

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