Conformational enantiodiscrimination for asymmetric construction of atropisomers

Shouyi Cen, Nini Huang, Dongsheng Lian, Ahui Shen, Mei-Xin Zhao () and Zhipeng Zhang ()
Additional contact information
Shouyi Cen: East China University of Science & Technology
Nini Huang: East China University of Science & Technology
Dongsheng Lian: East China University of Science & Technology
Ahui Shen: East China University of Science & Technology
Mei-Xin Zhao: East China University of Science & Technology
Zhipeng Zhang: East China University of Science & Technology

Nature Communications, 2022, vol. 13, issue 1, 1-7

Abstract: Abstract Molecular conformations induced by the rotation about single bonds play a crucial role in chemical transformations. Revealing the relationship between the conformations of chiral catalysts and the enantiodiscrimination is a formidable challenge due to the great difficulty in isolating the conformers. Herein, we report a chiral catalytic system composed of an achiral catalytically active unit and an axially chiral 1,1′-bi-2-naphthol (BINOL) unit which are connected via a C–O single bond. The two conformers of the catalyst induced by the rotation about the C–O bond, are determined via single-crystal X-ray diffraction and found to respectively lead to the formation of highly important axially chiral 1,1′-binaphthyl-2,2′-diamine (BINAM) and 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) derivatives in high yields (up to 98%), with excellent enantioselectivities (up to 98:2 e.r.) and opposite absolute configurations. The results highlight the importance of conformational dynamics of chiral catalysts in asymmetric catalysis.

Date: 2022
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-022-32432-8 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:13:y:2022:i:1:d:10.1038_s41467-022-32432-8

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

DOI: 10.1038/s41467-022-32432-8

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 ().