Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation

Prithwish Goswami, Sung Yeon Cho, Jin Hyun Park, Woo Hee Kim, Hyun Jin Kim, Myoung Hyeon Shin and Han Yong Bae ()
Additional contact information
Prithwish Goswami: Sungkyunkwan University
Sung Yeon Cho: Sungkyunkwan University
Jin Hyun Park: Sungkyunkwan University
Woo Hee Kim: Sungkyunkwan University
Hyun Jin Kim: Sungkyunkwan University
Myoung Hyeon Shin: Sungkyunkwan University
Han Yong Bae: Sungkyunkwan University

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

Abstract: Abstract A tetrasubstituted carbon atom connected by three sp3 or sp2-carbons with single nitrogen, i.e., the α-tertiary amine (ATA) functional group, is an essential structure of diverse naturally occurring alkaloids and pharmaceuticals. The synthetic approach toward ATA structures is intricate, therefore, a straightforward catalytic method has remained a substantial challenge. Here we show an efficient water-accelerated organocatalytic method to directly access ATA incorporating homoallylic amine structures by exploiting readily accessible general ketones as useful starting material. The synergistic action of a hydrophobic Brønsted acid in combination with a squaramide hydrogen-bonding donor under aqueous condition enabled the facile formation of the desired moiety. The developed exceptionally mild but powerful system facilitated a broad substrate scope, and enabled efficient multi-gram scalability.

Date: 2022
References: View complete reference list from CitEc
Citations: View citations in EconPapers (1)

Downloads: (external link)
https://www.nature.com/articles/s41467-022-30281-z 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_s41467-022-30281-z

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

DOI: 10.1038/s41467-022-30281-z

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 ().