reactions in water


Mlynarski, J.; Baś, S.
Catalytic Asymetric Aldol Reactions in Aqueous Media - 5 a Year Update
Chem. Soc. Rev. 2014 43 577-587 (link to page)


Mlynarski, J.; Paradowska, J.
Catalytic asymmetric aldol reactions in aqueous media
Chem. Soc. Rev. 2008 37 1502-1511


Asymmetric reactions in water and in aqueous solutions have become area of fast growing interest recently. Although for the long time neglected as a medium for organic reactions, water had to attract the attention as the most widely distributed solvent in the world. Indeed, water is the solvent used by nature for biological chemistry including aldol reaction being essential for glycolysis, gluconeogenesis and related processes. Consequently, artificial catalysts designed and used for aldol reaction in water can be either promising for the synthesis of enantiopure molecules and also important for the understanding of complex chemistry of life. This tutorial review summarized recent development in the area of aqueous asymmetric aldol reaction highlighting two fundamental directions - development of water compatible chiral Lewis acids and amine-based organocatalysts.


Woyciechowska, M.; Forcher, G.; Buda, S.; Mlynarski, J.
General Switch in Regioselectivity in the Mukaiyama Aldol Reaction of Silyloxyfuran with Aldehydes in Aqueous Solvents
Chem. Commun. 2012 48 11029-11031 (link to page)


Unexpected yet disciplined course of catalytic Mukaiyama-aldol reaction instead of expected vinylogous Mukaiyama-aldol reaction has been observed for the reaction of silyloxyfuran with various aldehydes under Lewis acid catalytic control in water-containing solvents.


Rogozińska, M.; Adamkiewicz, A.; Mlynarski, J.
Efficient “on water” organocatalytic protocol for the synthesis of optically pure warfarin anticoagulant
Green Chem.
2011 13 1155-1157 (link to page)


The present development leads to an efficient protocol for the “on water” formation of one of the most widely used anticoagulants warfarin: presented scalable and environmentally friendly organocatalytic approach affords target drug in optically pure form.


Paradowska, J.; Stodulski, M.; Mlynarski, J.
Asymmetric catalysis in water mediated by amino acids-based catalysts
Angew. Chem. Int. Ed. 2009 48 4288-4297


Wet and wild: Water is a powerful force in nature, as evident in the painting “ES” by Zdzislaw Beksinski (1985, oil, 92 cm×90 cm; reproduced with permission from Piotr Dmochowski), as well as a promising medium for asymmetric reactions. As catalysts, natural amino acids are ideal candidates. This Minireview summarizes recent advances in asymmetric catalysis in water, with amino acids and their derivatives as effective catalysts or essential components.