Issue 2, 2024

Primary activation of para-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Abstract

Demonstrated here is an asymmetric nucleophilic addition via primary activation of para-quinone methides (p-QMs) based on a chiral phosphoric acid catalytic system. In sharp contrast to previous CPA-based bifunctional activation processes that all required the nucleophiles to have an effective hydrogen bond donor unit (e.g., OH, NH), here no such unit is required in the nucleophile. N-protected indole nucleophiles were successfully utilized for the synthesis of chiral tetraarylmethanes with high efficiency and enantioselectivity under mild conditions. Therefore, this protocol significantly expanded the scope of asymmetric transformations of p-QMs.

Graphical abstract: Primary activation of para-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Sep 2023
Accepted
21 Nov 2023
First published
02 Dec 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 720-725

Primary activation of para-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Z. Han, B. Zhu, Y. Zang, C. Zhang, X. Dong, H. Huang and J. Sun, Chem. Sci., 2024, 15, 720 DOI: 10.1039/D3SC05014A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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