Organocatalytic atroposelective construction of axially chiral arylquinones

Shuai Zhu, Ye-Hui Chen, Yong-Bin Wang, Peiyuan Yu, Shao-Yu Li, Shao-Hua Xiang, Jun-Qi Wang, Jian Xiao and Bin Tan ()
Additional contact information
Shuai Zhu: Southern University of Science and Technology
Ye-Hui Chen: Southern University of Science and Technology
Yong-Bin Wang: Southern University of Science and Technology
Peiyuan Yu: Southern University of Science and Technology
Shao-Yu Li: Southern University of Science and Technology
Shao-Hua Xiang: Southern University of Science and Technology
Jun-Qi Wang: Southern University of Science and Technology
Jian Xiao: Qingdao Agricultural University
Bin Tan: Southern University of Science and Technology

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Atropisomeric biaryl motifs are ubiquitous in chiral catalysts and ligands. Numerous efficient strategies have been developed for the synthesis of axially chiral biaryls. In contrast, the asymmetric construction of o-quinone-aryl atropisomers has yet to be realized. Inspired by the rapid progress of the chemistry of biaryls, here we present our initial investigations about the atroposelective construction of axially chiral arylquinones by a bifunctional chiral phosphoric acid-catalyzed asymmetric conjugate addition and central-to-axial chirality conversion. With o-naphthoquinone as both the electrophile and the oxidant, three types of arylation counterparts, namely 2-naphthylamines, 2-naphthols and indoles, are utilized to assemble a series of atropisomeric scaffolds in good yields and excellent enantioselectivities. This approach not only expands the axially chiral library but also offers a route to a class of potential, chiral biomimetic catalysts.

Date: 2019
References: Add references at CitEc
Citations: View citations in EconPapers (1)

Downloads: (external link)
https://www.nature.com/articles/s41467-019-12269-4 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-12269-4

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-019-12269-4

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().