Diversity-oriented synthesis of P-stereogenic and axially chiral monodentate biaryl phosphines enabled by C-P bond cleavage

Liangzhi Pang, Zhan Huang, Qilin Sun, Gen Li, Jiaojiao Liu, Baoli Li, Congyue Ma, Jiaxu Guo, Chuanzhi Yao, Jie Yu () and Qiankun Li ()
Additional contact information
Liangzhi Pang: Anhui Agricultural University
Zhan Huang: Anhui Agricultural University
Qilin Sun: Anhui Agricultural University
Gen Li: Anhui Agricultural University
Jiaojiao Liu: Anhui Agricultural University
Baoli Li: Anhui Agricultural University
Congyue Ma: Anhui Agricultural University
Jiaxu Guo: Anhui Agricultural University
Chuanzhi Yao: Anhui Agricultural University
Jie Yu: Anhui Agricultural University
Qiankun Li: Anhui Agricultural University

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract Chiral monodentate biaryl phosphines (MOPs) have attracted intense attention as chiral ligands over the past decades. However, the creation of structurally diverse chiral MOPs with both P- and axial chirality is still in high demand but challenging. Here, we show a distinct strategy for diversity-oriented synthesis of structurally diverse MOPs containing both P- and axial chirality enabled by enantioselective C-P bond cleavage. The key chiral PdII intermediates, generated through the stereoselective oxidative addition of C-P bond, could be trapped by alkynes, R3Si-Bpin, diboron esters or reduced by H2O/B2pin2, leading to enantioenriched structurally diverse MOPs in excellent diastereo- and enantioselectivities. Based on the outstanding properties of the parent scaffolds, the P- and axially chiral monodentate biaryl phosphines serve as excellent catalysts in asymmetric [3 + 2] annulation of MBH carbonate affording the chiral functionalized bicyclic imide.

Date: 2023
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-023-40138-8 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:14:y:2023:i:1:d:10.1038_s41467-023-40138-8

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

DOI: 10.1038/s41467-023-40138-8

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 ().