1021394-84-2Relevant academic research and scientific papers
Tripeptides of the type H-D-Pro-Pro-Xaa-NH2 as catalysts for asymmetric 1,4-addition reactions: structural requirements for high catalytic efficiency
Wiesner, Markus,Neuburger, Markus,Wennemers, Helma
, p. 10103 - 10109 (2009)
Analysis of the structural and functional requirements within the asymmetric peptidic catalyst H-D-ProPro-Asp-NH2 led to the development of the closely related peptide H-D-ProPrO-Glu-NH2 as an even more efficient catalyst for asymmet
Surface-Improved Asymmetric Michael Addition Catalyzed by Amino Acids Adsorbed on Laponite
Sz?ll?si, Gy?rgy,Gombk?t?, Dániel,Mogyorós, Attila Zsolt,Fül?p, Ferenc
, p. 1992 - 2004 (2018/03/27)
An unprecedented enantioselectivity increase was observed in the presence of inorganic oxides in the asymmetric Michael addition of aldehydes to trans-β-nitrostyrene derivatives catalyzed by amino acids. The best results were reached in the l-proline cata
Efficient recovery and reuse of an immobilized peptidic organocatalyst
Arakawa, Yukihiro,Wiesner, Markus,Wennemers, Helma
supporting information; experimental part, p. 1201 - 1206 (2011/08/03)
Readily reusable immobilized organocatalysts are important from a practical, economic, and environmental viewpoint. However, their successful development has proven challenging and only limited reaction and recovery cycles have been achieved. We report an
Peptide-catalyzed conjugate addition reactions of aldehydes to nitroolefins
Wiesner, Markus,Wennemers, Helma
scheme or table, p. 1568 - 1571 (2010/10/20)
The tripeptide H-D-Pro-Pro-Glu-NH2 is an efficient catalyst for conjugate addition reactions of aldehydes to nitroolefins. Chiral γ-nitroaldehydes are obtained in excellent yields and stereoselectivities in the presence of as little as 1 mol% o
Enamine catalysis with low catalyst loadings - High efficiency via kinetic studies
Wiesner, Markus,Upert, Gregory,Angelici, Gaetano,Wennemers, Helma
supporting information; experimental part, p. 6 - 7 (2010/03/25)
(Chemical Equation Presented) Kinetic studies on enamine catalysis provided insight into the rate determining step(s) of peptide catalyzed conjugate addition reactions between aldehydes and nitroolefins. They demonstrate that not enamine formation but both the reaction of the enamine with the electrophile and hydrolysis of the resulting imine are rate limiting. These results allowed for reducing the catalyst loading by a factor of 10 to as little as 0.1 mol %. This is the lowest catalyst loading that has been achieved so far in enamine catalysis with low molecular weight catalysts for a broad range of substrates.
Tripeptides as efficient asymmetric catalysts for 1,4-addition reactions of aldehydes to nitroolefins - A rational approach
Wiesner, Markus,Revell, Jefferson D.,Wennemers, Helma
, p. 1871 - 1874 (2008/12/22)
(Chemical Equation Presented) Bridging the gap: Conformational analysis of a peptidic catalyst for aldol reactions led to the development of H-D-Pro-Pro-Asp-NH2 as a highly efficient catalyst for conjugate addition reactions between aldehydes a
