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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
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
,
Jiahao Liu
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
,
Zhe Wang
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
,
Terumasa Kato
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
b   Guangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
c   Laboratory of Organocatalytic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
,
Yan Liu∗
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
b   Guangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
,
Keiji Maruoka∗
a   School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
b   Guangdong Provincial Key Laboratory of Plant Resouces Biorefinery, Guangdong University of Technology, Guangzhou, 510006, P. R. of China
c   Laboratory of Organocatalytic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
› Author AffiliationsWe are grateful for the financial support from the National Natural Science Foundation of China (Nos. 21977019, 22101053, 22050410279, 22250710134), the Guangdong Provincial Key Laboratory of Plant Resources Biorefinery (2021B1212040011), and the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant JP21H05026).
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Dedicated to the 80th 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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2065-3962.
  • Supporting Information


Publication History

Received: 05 March 2023

Accepted after revision: 29 March 2023

Accepted Manuscript online:
29 March 2023

Article published online:
09 May 2023

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