Atroposelective synthesis of biaxial bridged eight-membered terphenyls via a Co/SPDO-catalyzed aerobic oxidative coupling/desymmetrization of phenols

Shuang-Hu Wang, Shi-Qiang Wei, Ye Zhang, Xiao-Ming Zhang, Shu-Yu Zhang, Kun-Long Dai, Yong-Qiang Tu (), Ka Lu and Tong-Mei Ding
Additional contact information
Shuang-Hu Wang: Shanghai Jiao Tong University
Shi-Qiang Wei: Shanghai Jiao Tong University
Ye Zhang: Shanghai Jiao Tong University
Xiao-Ming Zhang: Lanzhou University
Shu-Yu Zhang: Shanghai Jiao Tong University
Kun-Long Dai: Shanghai Jiao Tong University
Yong-Qiang Tu: Shanghai Jiao Tong University
Ka Lu: Lanzhou University
Tong-Mei Ding: Shanghai Jiao Tong University

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Bridged chiral biaryls are axially chiral compounds with a medium-sized ring connecting the two arenes. Compared with plentiful methods for the enantioselective synthesis of biaryl compounds, synthetic approaches for this subclass of bridged atropisomers are limited. Here we show an atroposelective synthesis of 1,3-diaxial bridged eight-membered terphenyl atropisomers through an Co/SPDO (spirocyclic pyrrolidine oxazoline)-catalyzed aerobic oxidative coupling/desymmetrization reaction of prochiral phenols. This catalytic desymmetric process is enabled by combination of an earth-abundant Co(OAc)2 and a unique SPDO ligand in the presence of DABCO (1,4-diaza[2.2.2]bicyclooctane). An array of diaxial bridged terphenyls embedded in an azocane can be accessed in high yields (up to 99%) with excellent enantio- (>99% ee) and diastereoselectivities (>20:1 dr).

Date: 2024
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-024-48858-1 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:15:y:2024:i:1:d:10.1038_s41467-024-48858-1

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

DOI: 10.1038/s41467-024-48858-1

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 ().