2014
DOI: 10.1038/ncomms4884
|View full text |Cite
|
Sign up to set email alerts
|

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

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 a… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
21
0

Year Published

2014
2014
2024
2024

Publication Types

Select...
6

Relationship

2
4

Authors

Journals

citations
Cited by 20 publications
(21 citation statements)
references
References 20 publications
0
21
0
Order By: Relevance
“…(1)]. [3] Herein, we report an unexpected formation of ; EWG = electron-withdrawing group] and 2,5-dihydrofurans [Eq. (2); M.S.…”
Section: Wu Fan and Shengming Ma*mentioning
confidence: 99%
See 3 more Smart Citations
“…(1)]. [3] Herein, we report an unexpected formation of ; EWG = electron-withdrawing group] and 2,5-dihydrofurans [Eq. (2); M.S.…”
Section: Wu Fan and Shengming Ma*mentioning
confidence: 99%
“…

A novel copper(I)-catalyzed three-component reaction for the efficient synthesis of 3-amino-2-pyrones and 2,5dihydrofurans from propargyl alcohols, aldehydes, and amines has been developed. [3] Herein, we report an unexpected formation of 3-amino-2pyrones [Eq. Through mechanistic studies, it is believed that the three-component reaction consists of an A 3 -coupling to propargylic amine, alkyne-allene isomerization, and intramolecular cyclization of the allenol to form a furan.

…”
mentioning
confidence: 99%
See 2 more Smart Citations
“…The A 3 coupling (Scheme 4) has been widely studied in recent years [57][58][59][60][61], as the resulting propargylamines have been proposed as key intermediates in the synthesis of various N-containing biologically active compounds [62][63][64][65]. Even though many metal sources and compounds, including CPs [66][67][68][69], have been tested as catalysts for this reaction, Cu(II) CPs have been used very rarely [34].…”
Section: Catalytic Studiesmentioning
confidence: 99%