Beilstein J. Org. Chem.2016,12, 2563–2569, doi:10.3762/bjoc.12.251
. 26, Saint Petersburg, 198504, Russia 10.3762/bjoc.12.251 Abstract 2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones
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Graphical Abstract
Scheme 1:
The regioselectivities of the reaction between monosubstituted thioureas and maleimides according t...
Beilstein J. Org. Chem.2016,12, 918–936, doi:10.3762/bjoc.12.90
the main focus has been directed not only to the search for new efficient chiral catalysts, but also to the development of efficient pronucleophiles. This review highlights the utility and first examples of 1H-imidazol-4(5H)-ones and thiazol-4(5H)-ones as pronucleophiles in catalytic asymmetric
reactions.
Keywords: asymmetric catalysis; bifunctional catalysts; 1H-imidazol-4(5H)-ones; pronucleophiles; thiazol-4(5H)-ones; Introduction
Asymmetric catalysis [1][2][3] constitutes a very powerful tool for the preparation of enantiomerically pure compounds [4]. Recent efforts in the field have been
-additions to allenic ketones and esters [35][36], 1,6-additions to conjugated dienones [37], aldol/Mannich reactions [26][38][39][40], α-sulfenylation reactions [41] and alkylations [42][43]. More recently the nitrogen (1H-imidazol-4(5H)-ones, Figure 1b, X = NR’) and sulfur (thiazol-4(5H)-ones, Figure 1b, X
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Graphical Abstract
Figure 1:
Some α-substituted heterocycles for asymmetric catalysis, their reactivity patterns against enoliza...