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Gold(III)‐Catalysed cis‐to‐trans Cyclopropyl Isomerization.

Authors :
Reiersølmoen, Ann Christin
Østrem, Elise
Fiksdahl, Anne
Source :
European Journal of Organic Chemistry. 7/6/2018, Vol. 2018 Issue 25, p3317-3325. 9p.
Publication Year :
2018

Abstract

Novel chiral gold(III) complexes, based on bisoxazoline (BOX) and 2‐pyridyl‐(–)menthol ligands, were prepared and characterised (X‐ray), and their catalytic properties in cyclopropanation reactions of propargyl esters with alkenes were explored. The BOX‐AuIII catalysts gave excellent results for fast cyclopropanation and subsequent in situ cis‐to‐trans vinylcyclopropyl isomerization. AuI and AuIII catalytic species showed different abilities to tune the reactions and transform the initially formed cis product into the isomerized trans product. The appropriate choice of gold(I) or gold(III) complex enabled highly stereoselective formation of cis or trans products (up to 99 % dr), in high yields (63–98 %). The pure cis isomers were used in isomerization studies, showing that rapid cis‐to‐trans isomerization took place at room temperature in the presence of BOX‐AuIII catalysts. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
1434193X
Volume :
2018
Issue :
25
Database :
Academic Search Index
Journal :
European Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
130547748
Full Text :
https://doi.org/10.1002/ejoc.201800419