55848-19-6Relevant articles and documents
Tetrahedral boronates as basic catalysts in the aldol reaction
Müller, Tobias,Djanashvili, Kristina,Peters, Joop A.,Arends, Isabel W.C.E.,Hanefeld, Ulf
, p. 587 - 595 (2016/02/12)
β-Hydroxyketones are versatile building blocks in organic synthesis, which can be conveniently synthesized from ketones and aldehydes by aldol reactions. Unfortunately, these reactions often suffer from dehydration of the initially formed β-hydroxyketones
Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones
Clarke, Sarah L.,McSweeney, Christina M.,McGlacken, Gerard P.
, p. 356 - 361 (2014/04/03)
A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity.
Iron- and bismuth-catalyzed asymmetric mukaiyama aldol reactions in aqueous media
Kitanosono, Taku,Ollevier, Thierry,Kobayashi, Shu
supporting information, p. 3051 - 3062 (2014/01/06)
We have developed asymmetric Mukaiyama aldol reactions of silicon enolates with aldehydes catalyzed by chiral FeII and BiIII complexes. Although previous reactions often required relatively harsh conditions, such as strictly anhydrous conditions, very low temperatures (-78 °C), etc., the reactions reported herein proceeded in the presence of water at 0 °C. To find appropriate chiral water-compatible Lewis acids for the Mukaiyama aldol reaction, many Lewis acids were screened in combination with chiral bipyridine L1, which had previously been found to be a suitable chiral ligand in aqueous media. Three types of chiral catalysts that consisted of a FeII or BiIII metal salt, a chiral ligand (L1), and an additive have been discovered and a wide variety of substrates (silicon enolates and aldehydes) reacted to afford the desired aldol products in high yields with high diastereo- and enantioselectivities through an appropriate selection of one of the three catalytic systems. Mechanistic studies elucidated the coordination environments around the FeII and BiIII centers and the effect of additives on the chiral catalysis. Notably, both Bronsted acids and bases worked as efficient additives in the Fe II-catalyzed reactions. The assumed catalytic cycle and transition states indicated important roles of water in these efficient asymmetric Mukaiyama aldol reactions in aqueous media with the broadly applicable and versatile catalytic systems. Copyright
