Unexpected E-stereoselective reductive A3-coupling reaction of terminal alkynes with aldehydes and amines

Wu Fan, Weiming Yuan and Shengming Ma ()
Additional contact information
Wu Fan: Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University
Weiming Yuan: Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University
Shengming Ma: Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University

Nature Communications, 2014, vol. 5, issue 1, 1-9

Abstract: Abstract The transition-metal catalysed three-component coupling of an alkyne, an aldehyde and an amine has been became a widely used method for preparing propargylic amines. Here, we report an unexpected copper(I)-catalysed E-stereoselective reduction of propargylic amines in situ formed from readily available terminal alkynes, aldehydes and 3-pyrroline or isoindoline via [1,5]-hydride transfer, affording E-allylic amines. Through mechanistic studies, it is believed that the unsaturated cyclic dialkylamine is acting as hydrogen donor.

Date: 2014
References: Add references at CitEc
Citations: View citations in EconPapers (1)

Downloads: (external link)
https://www.nature.com/articles/ncomms4884 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:5:y:2014:i:1:d:10.1038_ncomms4884

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

DOI: 10.1038/ncomms4884

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 ().