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State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China.
Published: February 2023
AI Article Synopsis
The study explores a new method for creating chiral cyclopropanes through a safer catalytic asymmetric cyclopropanation reaction that uses 1,2-dicarbonyl compounds instead of hazardous diazo compounds.
This method employs simple chiral salen-Mo catalysts, achieving good enantioselectivities and yields across various substrates.
The research suggests that a specific Mo(III) species is vital to the catalytic process, offering insights into the future applications of chiral salen-Mo complexes in asymmetric catalysis.
Article Abstract
The catalytic asymmetric cyclopropanation reaction of alkenes with diazo compounds is a direct and powerful method to construct chiral cyclopropanes that are essential to drug discovery. However, diazo compounds are potentially explosive and often require hazardous reagents for their preparation. Here, we report on the use of 1,2-dicarbonyl compounds as safe and readily available surrogates for diazo compounds in the direct catalytic asymmetric deoxygenative cyclopropanation reaction. Enabled by a class of simple and readily accessible chiral salen-Mo catalysts, the reaction proceeded with generally good enantioselectivities and yields toward a wide range of substrates (80 examples). Preliminary mechanistic studies suggested that the proposed μ-oxo bridged dinuclear Mo(III)-species was the catalytically active species. This strategy not only provides a promising route for the synthesis of chiral cyclopropanes but also opens a new window for the potential applications of chiral salen-Mo complexes in asymmetric catalysis.
