Syntheses of α-CF3-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

Kyu Terashima; Tomoko Kawasaki-Takasuka; Tomohiro Agou; Toshio Kubota; Takashi Yamazaki

doi:10.1039/D0OB00951B

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Syntheses of α-CF₃-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers†

Kyu Terashima,^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

New and successful results for the construction of new and structurally interesting compounds are reported via N-heterocyclic carbene (NHC)-catalyzed 1,6-conjugate additions of a variety of aldehydes to δ-CF₃-δ-substituted p-quinone methides generated in situ, and the products are used for the 1,2-addition reactions of appropriate metal nucleophiles, enabling us to furnish highly diastereoselective products with a unique successive quaternary carbon-tertiary alcohol framework (up to dr = >99 : 1).

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Article information

DOI: https://doi.org/10.1039/D0OB00951B
Article type: Paper
Submitted: 08 May 2020
Accepted: 03 Jun 2020
First published: 04 Jun 2020

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Org. Biomol. Chem., 2020,18, 4638-4644

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Syntheses of α-CF₃-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

K. Terashima, T. Kawasaki-Takasuka, T. Agou, T. Kubota and T. Yamazaki, Org. Biomol. Chem., 2020, 18, 4638 DOI: 10.1039/D0OB00951B

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Organic & Biomolecular Chemistry