In this communication, we designed a highly selective camphor sulfonyl functionalized crown-ether-tethered calix[4]arene-derived organocatalyst for asymmetric Strecker reaction to provide the desired cyano adducts in high yields (∼99.9% yield) and enantioselectivities (up to 99.3% ee). Furthermore, 2 step facile syntheses of the antiplatelet drug ()-clopidogrel exemplify the potential of this method for the preparation of commercial compounds.
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http://dx.doi.org/10.1039/d4cc02674h | DOI Listing |
Inorg Chem
December 2024
Department of Chemistry, Indian Institute of Technology Patna, Patna, Bihar 801106, India.
Nucleobase adenine is a promising candidate for synthesizing fascinating coordination polymers (CPs) due to the presence of five potential metal-ion binding centers. In recent years, CPs have emerged as promising Lewis acid-base centers containing heterogeneous catalysts for a wide range of organic transformations. However, the crucial role of stoichiometric regulations of the starting materials and their consequential impact on catalytic performance are rarely studied.
View Article and Find Full Text PDFJ Am Chem Soc
September 2024
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science Westlake University, 600 Dunyu Road, Hangzhou 310030, China.
α-Aminonitriles are not only broadly useful building blocks but also structural motifs in bioactive molecules. The Strecker reaction is one of the most widely used methods for α-aminonitrile synthesis. However, a severe drawback in Strecker reactions is the required use of a stoichiometric amount of toxic cyanation reagents.
View Article and Find Full Text PDFChem Commun (Camb)
August 2024
Sustainable Materials and Catalysis Research Laboratory (SMCRL), Department of Chemistry, Indian Institute of Technology Jodhpur, Jodhpur-342037, India.
In this communication, we designed a highly selective camphor sulfonyl functionalized crown-ether-tethered calix[4]arene-derived organocatalyst for asymmetric Strecker reaction to provide the desired cyano adducts in high yields (∼99.9% yield) and enantioselectivities (up to 99.3% ee).
View Article and Find Full Text PDFChem Sci
April 2024
Department of Industrial Chemistry "Toso Montanari", Center for Chemical Catalysis C3 & INSTM RU Bologna V. Gobetti 85 40129 Bologna Italy
Organocatalytic asymmetric synthesis has evolved over the years and continues to attract the interest of many researchers worldwide. Enantiopure noncanonical amino acids (ncAAs) are valuable building blocks in organic synthesis, medicinal chemistry, and chemical biology. They are employed in the elaboration of peptides and proteins with enhanced activities and/or improved properties compared to their natural counterparts, as chiral catalysts, in chiral ligand design, and as chiral building blocks for asymmetric syntheses of complex molecules, including natural products.
View Article and Find Full Text PDFJ Am Chem Soc
May 2024
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science, Westlake University; 600 Dunyu Road, Hangzhou 310030, China.
Chiral aminonitriles not only are broadly useful building blocks but also increasingly appear as structural motifs in bioactive molecules and pharmaceuticals. The catalytic asymmetric synthesis of chiral aminonitriles, therefore, has been intensively investigated, as reflected in numerous reports of catalytic asymmetric Strecker reactions. Despite such great progress, the catalytic asymmetric synthesis of chiral α,α-dialkyl aminonitriles in a highly selective and efficient manner is still a formidable challenge.
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