Biomimetic Asymmetric Reduction of Tetrasubstituted Olefin 2,3-Disubstituted Inden-1-ones with Chiral and Regenerable NAD(P)H Model CYNAM
Zhou‐Hao Zhu, Yi‐Xuan Ding, Bo Wu, Yong‐Gui Zhou
Abstract
Because of the formidable development of the asymmetric reduction of tetrasubstituted olefins, an effective method is in urgent demand. Herein, through the biomimetic protocol of the coenzyme NAD(P)H, the reduction of tetrasubstituted olefin 2,3-substituted 1H-inden-1-ones has been successfully realized with the catalytic chiral NAD(P)H model CYNAM, which is hard to bring about via the common rhodium or iridium-based catalytic system, producing the corresponding products in good yield (up to 98%) with good enantioselectivity (up to 99% ee). Furthermore, the chiral bioactive molecule can be concisely synthesized from the reduced product.
Topics & Concepts
ChemistryNAD+ kinaseOlefin fiberYield (engineering)CatalysisCombinatorial chemistryReduction (mathematics)RhodiumEnantioselective synthesisStereochemistryOrganic chemistryEnzymeMaterials scienceMathematicsMetallurgyGeometryAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisCarbon dioxide utilization in catalysis