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

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

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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

Key words

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

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Supplementary Material

Supplementary Material

Supporting Information