Organocatalytic enantioselective construction of mono- and polycyclic structures by domino reactions

Abstract

In this manuscript, we are particularly interested in the formation of chiral mono- and polycyclic compounds by organocatalytic domino reactions. In order to understand better the studied reactivities, some generalities about the activation modes used during this work, aminocatalysis and bifunctional thiourea-type catalysis, are firlsty introduced. Afterwards, a study on the synthesis of chiral γ-butenolides from renewable sources by a direct vinyligous Michael addition of Angelicalactone to enals catalysed by an aminal-pyrrolidine catalyst is reported. In the third part, we focused on the reactivity of acyclic 1,2-diketones in organocatalytic domino transformations. Interesting chiral polysubstituted cyclopentanones are synthesized by domino reactions. Finally, β,γ-unsaturated 1,2 dicarbonyl compounds are involved in organocatalytic domino tranformations as bis-electrophiles with various cyclic 1,3-ketoesters forming interesting chiral polysubstituted bicyclo[3.2.1]octanones.