1131711-83-5Relevant articles and documents
Induced chirality in a metal-organic framework by postsynthetic modification for highly selective asymmetric aldol reactions
Demuynck, Anneleen L.W.,Goesten, Maarten G.,Ramos-Fernandez, Enrique V.,Dusselier, Michiel,Vanderleyden, Jozef,Kapteijn, Freek,Gascon, Jorge,Sels, Bert F.
, p. 2211 - 2214 (2014)
A straightforward synthetic route to chiral metal-organic frameworks is proposed that relies on an acid-base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.
Asymmetric aldol reaction catalyzed by modularly designed organocatalysts
Sinha, Debarshi,Mandal, Tanmay,Gogoi, Sanjib,Goldman, Joshua J.,Zhao, John Cong-Gui
, p. 2624 - 2630 (2013/01/15)
The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for cata
Solid acids as heterogeneous support for primary amino acid-derived diamines in direct asymmetric aldol reactions
Demuynck, Anneleen L. W.,Peng, Li,De-Clippel, Filip,Vanderleyden, Jozef,Jacobs, Pierre A.,Sels, Bert F.
supporting information; experimental part, p. 725 - 732 (2011/05/08)
We have achieved the non-covalent immobilization of chiral primary amino acid-derived diamines on organic and inorganic sulfonated solid acids through acid-base interaction. With the commercial sulfonated fluoropolymer nafion NR50 as support an optimal ba
Direct asymmetric syn-aldol reactions of linear aliphatic ketones with primary amino acid-derived diamines
Demuynck, Anneleen L. W.,Vanderleyden, Jozef,Sels, Bert F.
experimental part, p. 2421 - 2426 (2010/12/25)
We have designed a novel class of chiral diamine organocatalysts based on natural primary amino acids that efficiently catalyze syn-selective aldol reactions of challenging linear ketones, such as 2-butanone, and aromatic aldehydes. In the presence of trifluoroacetic acid (TFA) as Bronsted acid and 2,4-dinitrophenol (DNP) as co-catalyst, syn-aldol products have been obtained with excellent enantioselectivities of up to> 99% ee.
2,4-Dinitrophenol as an effective cocatalyst: Greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions
Da, Chao-Shan,Che, Li-Ping,Guo, Qi-Peng,Wu, Feng-Chun,Xiao, Ma.,Jia, Ya-Ning
experimental part, p. 2541 - 2546 (2009/08/07)
Seven primary amine organocatalysts 1a-g were readily prepared from natural primary amino acids via two steps and then were used to catalyze the direct asymmetric aldol reaction, but they showed very poor enantioselectivities and activities. As an effective cocatalyst, 2,4-dinitrophenol (DNP) dramatically elevated the activities and enantioselectivities of these very inefficient primary amine organocatalysts. This remedial course to the very inefficient organocatalysts by selection and employment of the optimal cocatalyst was particularly cost-effective and environment-beneficial compared with de novo development of catalysts. The highest efficient organocatalytic system that was composed of If and DNP showed high enantioselectivities and good to high diastereoselectivities with a broad spectrum of seven ketones. The linear ketones and cyclopentanone got predominant syn products whereas cyclohexanone mainly gave anti products.
