An enantioselective [3+2] cycloaddition of vinyl cyclopropane derived from 1,3-indanedione with nitroalkenes catalyzed by palladium(0) with a chiral bis(tert-amine) ligand was developed in high yields with good diastereoselectivities and excellent enantioselectivities. The resulting bis(tert-amine)-palladium complex proved to be a highly efficient catalyst for this cycloaddition.
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http://dx.doi.org/10.1002/chem.201405407 | DOI Listing |
Chemistry
January 2025
Karlsruhe Institute of Technology, Institute for biological interfaces 1 (IBG-1), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, GERMANY.
Enantioselectivity is a key advantage of enzymatic catalysis. Understanding the most important factors influencing enantioselectivity necessitates thorough investigation for each specific enzyme. In this study, we explore various approaches to optimize reaction conditions for organosilicon production using an immobilized Cytochrome C recently tailored via directed evolution.
View Article and Find Full Text PDFChem Rec
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
Since the introduction of the concept of inherent chirality by Böhmer, an important part of research focused on the asymmetric synthesis of calixarene macrocycles. However, long synthetic procedures and tedious separation strategies hampered the application of this technology in many topics of organic chemistry, including enantioselective molecular recognition and catalysis. Very recently, a new generation of enantioselective catalytic methodologies has been reported, able to provide highly functionalized, inherently chiral calixarenes in a straightforward manner.
View Article and Find Full Text PDFNat Chem
January 2025
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, China.
The substitution of an aromatic ring with a C(sp)-rich bicyclic hydrocarbon, known as bioisosteric replacement, plays a crucial role in modern drug discovery. Substituted bicyclo[1.1.
View Article and Find Full Text PDFNat Commun
January 2025
State Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, PR China.
Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity. This catalytic reaction can not only be applied to aryl chlorides/bromides, which are challenging to access by other means, but also to benzyl chlorides containing silicon groups. Additionally, the absence of a sacrificial anode lays a foundation for scalability.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
University of Toronto, Dept. of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.
A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.
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