Header

UZH-Logo

Maintenance Infos

Chemoselective trifluoromethylation of the C=N group of alpha-iminoketones derived from arylglyoxals


Obijalska, Emilia; Kowalski, Marcin K; Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (2014). Chemoselective trifluoromethylation of the C=N group of alpha-iminoketones derived from arylglyoxals. Journal of Fluorine Chemistry, 168:151-157.

Abstract

Chemoselective addition of (trifluoromethyl)trimethylsilane to the C=N group of N-(tert-butyl)-alpha-iminoketones in the presence of a fluoride ion as a catalyst was achieved under acidic conditions. Subsequent diastereoselective reductions of the obtained alpha-amino-alpha-(trifluoromethyl)ketones led to beta-amino-beta-(trifluoromethyl) alcohols in very good yields and high diastereoselectivities. Different reducing agents were tested; the reduction performed with LiAlH4 and Raney-Ni, respectively, afforded the desired diastereoisomers in a reversed ratio.

Abstract

Chemoselective addition of (trifluoromethyl)trimethylsilane to the C=N group of N-(tert-butyl)-alpha-iminoketones in the presence of a fluoride ion as a catalyst was achieved under acidic conditions. Subsequent diastereoselective reductions of the obtained alpha-amino-alpha-(trifluoromethyl)ketones led to beta-amino-beta-(trifluoromethyl) alcohols in very good yields and high diastereoselectivities. Different reducing agents were tested; the reduction performed with LiAlH4 and Raney-Ni, respectively, afforded the desired diastereoisomers in a reversed ratio.

Statistics

Citations

2 citations in Web of Science®
2 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

51 downloads since deposited on 16 Oct 2014
17 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:16 Oct 2014 11:10
Last Modified:09 Dec 2017 15:46
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (PL-Cracow)
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2014.09.002

Download