Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/35695
Title: Silver-catalyzed transformation of propargylic Amine N-Oxides to Enones and Acyloxy ketones via Isoxazolinium intermediates
Authors: Cui, JF
Kung, KKY
Ko, HM
Hui, TW
Wong, MK 
Keywords: Isoxazolinium salts
N-oxides
Peptide modification
Propargylic amines
Silver catalysis
Issue Date: 2014
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2014, v. 356, no. 14-15, p. 2965-2973 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: A novel silver-catalyzed transformation of propargylic amine N-oxides with switchable product profiles has been developed. A diversity of enones with excellent E/Z ratios (up to > 20: 1) were obtained when the reactions were conducted in aprotic solvents. In contrast, 3-chlorobenzoxymethyl ketones and alpha-(3-chloro)-benzoxy enones were obtained by using protic solvents. Mechanistic studies suggested that in situ generated isoxazolinium ions are the key intermediates involved in these novel silver-catalyzed reaction pathways. Applications on the chemoselective modification of cysteine-containing peptides in aqueous medium have also been achieved.
URI: http://hdl.handle.net/10397/35695
ISSN: 1615-4150 (print)
1615-4169 (online)
DOI: 10.1002/adsc.201400395
Appears in Collections:Journal/Magazine Article

Access
View full-text via PolyU eLinks SFX Query
Show full item record

SCOPUSTM   
Citations

11
Last Week
0
Last month
2
Citations as of Mar 19, 2017

WEB OF SCIENCETM
Citations

7
Last Week
0
Last month
1
Citations as of Mar 23, 2017

Page view(s)

24
Last Week
1
Last month
Checked on Mar 19, 2017

Google ScholarTM

Check

Altmetric



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.