Design of Y-Shaped Trimers of Chiral Phase-Transfer Catalysts for the Asymmetric Alkylation of Amino Acid Derivatives

Shengyu Yu; Jiahao Liu; Zhe Wang; Terumasa Kato; Yan Liu; Keiji Maruoka

doi:10.1055/a-2065-3962

Synlett, Table of Contents

Synlett 2023; 34(20): 2388-2392
DOI: 10.1055/a-2065-3962

cluster

Special Issue Dedicated to Prof. Hisashi Yamamoto

Design of Y-Shaped Trimers of Chiral Phase-Transfer Catalysts for the Asymmetric Alkylation of Amino Acid Derivatives

Shengyu Yu

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

,

Jiahao Liu

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

,

Zhe Wang

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

,

Terumasa Kato

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

^bGuangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

^cLaboratory of Organocatalytic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan

,

Yan Liu∗

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

^bGuangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

,

Keiji Maruoka∗

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

^bGuangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China

^cLaboratory of Organocatalytic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan

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Abstract

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Dedicated to the 80^th birthday of Prof. Hisashi Yamamoto

Abstract

A series of soluble Y-shaped trimers of chiral phase-transfer catalysts were synthesized and utilized in the asymmetric alkylation of amino acid Schiff bases. The length of the linker between the ammonium cation of the simplified Maruoka catalyst and a phloroglucinol moiety was varied and excellent yields and enantioselectivity were observed when using the Y-shaped trimer of chiral phase-transfer catalyst with an octamethylene linker. A theoretical study of the most efficient Y-shaped trimer of chiral phase-transfer catalyst suggests the chiral ammonium center of the catalyst is more exposed and thus more available in the reaction.

Key words

Y-shaped trimer - chiral phase-transfer catalyst - asymmetric alkylation - amino acid - theoretical study

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References

References and Notes

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