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Synthesis 2023; 55(22): 3851-3861
DOI: 10.1055/a-2122-3731
DOI: 10.1055/a-2122-3731
paper
Direct Organocatalytic Asymmetric para C–H Aminoalkylation of Aniline Derivatives Affording Diarylmethylamines
This work was supported by the Innovation Fund (2019A005), the NSFC (22071147 and 81872418), Shanghai Scientific and Technological Innovation Action Plan (21S11902000), and the Transforming Medicine Cross Research Fund of Shanghai Jiao Tong University (YG2022QN032).
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2122-3731.
- Supporting Information
Publication History
Received: 09 May 2023
Accepted after revision: 03 July 2023
Accepted Manuscript online:
04 July 2023
Article published online:
16 August 2023
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For selected examples of asymmetric synthesis of chiral diarylmethylamines through imine addition, see:
For para C–H functionalization of aniline derivatives, see: