Direct Organocatalytic Asymmetric para C–H Aminoalkylation of Aniline Derivatives Affording Diarylmethylamines

Cheng-Long Wang; Yong-Ling Li; Le Wang; Xun-Hui Wang; Jia Zhou; He-Yuan Bai; Tong-Mei Ding; Zhen-Liang Sun

doi:10.1055/a-2122-3731

Synthesis, Table of Contents

Synthesis 2023; 55(22): 3851-3861
DOI: 10.1055/a-2122-3731

paper

Direct Organocatalytic Asymmetric para C–H Aminoalkylation of Aniline Derivatives Affording Diarylmethylamines

Authors

Cheng-Long Wang‡

^aSchool of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. of China

^bAffiliated Fengxian Hospital, Southern Medical University, Shanghai 201499, P. R. of China
Yong-Ling Li‡

^aSchool of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. of China
Le Wang

^cSchool of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
Xun-Hui Wang

^cSchool of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
Jia Zhou

^cSchool of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
He-Yuan Bai

^cSchool of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
Tong-Mei Ding∗

^cSchool of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
Zhen-Liang Sun∗

^bAffiliated Fengxian Hospital, Southern Medical University, Shanghai 201499, P. R. of China

Abstract

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Abstract

An efficient method to directly catalyze asymmetric para C–H aminoalkylation of aniline derivatives to prepare chiral diarylmethylamine system was developed. Aniline derivatives underwent an enantioselective aminoalkylation in the presence of chiral phosphoric acid, affording a series of optically active diarylmethylamine products in good yields and enantioselectivities (73% yield, 91% ee). Furthermore, this method could be used to prepare the key intermediate of chiral drug levocetirizine.

Key words

organic catalysis - aniline derivative - aminoalkylation - diarylmethylamine - asymmetric synthesis

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References

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Supplementary Material

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