Title
Thiourea derivatives of Troger's base: synthesis, enantioseparation and evaluation in organocatalysis of Michael addition to nitroolefins
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
,
Subject
Chemistry
Source (journal)
Arkivoc : online journal of organic chemistry. - Place of publication unknown, 2000, currens
Volume/pages
(2009) :Part 14 , p. 124-134
ISSN
1551-7004
1424-6369
ISI
000277913400012
Carrier
E
Target language
English (eng)
Affiliation
University of Antwerp
Abstract
The catalytic activity of racemic thiourea derivatives of Troger's base (+/-)-2-4 in Michael additions of malonate derivatives to trans-beta-nitrostyrene was studied. Due to the low basicity of Troger's base, the outcome of the addition reactions was strongly dependent on the pK(a) of the nucleophile. Thiourea catalysts (+/-)-2, 3 were resolved on the chiral stationary phase Whelk O1. Unfortunately, enantiopure catalysts 2 and 3 showed no stereoselectivity in the Michael addition.
Full text (open access)
https://repository.uantwerpen.be/docman/irua/698c5c/7519.pdf
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