A general evaluation of silylated nucleophiles to intercept transient α-oxoketenes generated by microwave-assisted Wolff rearrangement of 2-diazo-1,3-dicarbonyl compounds is presented. Original scaffolds and synthetic intermediates are accessed in a rapid, efficient and easy-to-handle way. Mechanistic studies by DFT calculations and some post-functionalizations are discussed.
Tetrahydropyridines are important heterocycles present in many molecules of natural and non‐natural origins that exhibit a wide array of biological activities. With several sp3‐hybridized carbon atoms in their structure, they often include one or several stereogenic centers, whose control represents a great synthetic challenge. For the past two decades, enantioselective organocatalysis has developed as a very powerful strategy to perform the synthesis of enantioenriched compounds, including heterocycles. In this Microreview, we wish to provide the readers with a general overview about the organocatalytic strategies that have been used to achieve the preparation of diversified families of tetrahydropyridines, thereby providing elements of reflection for further developments.
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