Experimental and Theoretical Studies in Hydrogen-Bonding Organocatalysis.
Chiral thioureas and squaramides are among the most prominent hydrogen-bond bifunctional organocatalysts now extensively used for various transformations, including aldol, Michael, Mannich and Diels-Alder reactions. More importantly, the experimental and computational study of the mode of activation has begun to attract considerable attention. Various experimental, spectroscopic and calculation methods are now frequently used, often as an integrated approach, to establish the reaction mechanism, the mode of activation or explain the stereochemical outcome of the reaction. This article comprises several case studies, sorted according to the method used in their study. The aim of this review is to give the investigators an overview of the methods currently utilized for mechanistic investigations in hydrogen-bonding organocatalysis.
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, Bratislava SK-842 15, Slovakia. zabka.matej@gmail.com.
Matej
M
Žabka
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, Bratislava SK-842 15, Slovakia. radovan.sebesta@fns.uniba.sk.
Radovan
R
Šebesta
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D019295:Computational Biology / Q000379:methods*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008962:Models, Theoretical; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000577:Amides; D013890:Thiourea
experimental and computational studies; hydrogen bonding; organocatalysis; reaction mechanisms; squaramide; thiourea