Synthesis of Chiral Cyclopentenones

Abstract

The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks.

Co‐Cluster‐Based Metal–Organic Frameworks as Selective Catalysts for Benzene Tandem Acylation–Nazarov Cyclization to Benzocyclopentanone

“…We have explored MOF‐based catalysts for tandem acylation–Nazarov cyclization reactions . The reaction is an acid‐catalyzed acylation followed by 4π‐electrocyclic process to build a new carbon–carbon bond for the synthesis of cyclopentenone, which is the key intermediate in the synthesis of numerous biologically active molecules and highly functional compounds . Recently, on the basis of the high catalytic activity, robustness, and excellent selectivity of MOF‐based catalysts, we have reported highly efficient Zn‐MOF and Ag‐MOF for the synthesis of cyclopenta[ b ]pyrroles by treatment of pyrrole derivatives with α,β‐unsaturated carboxylic acids .…”

A Straightforward Approach to the Synthesis of Disubstituted Cyclopentenones

“…In the case of small five‐membered rings, the cyclopentenone moiety is present in a large amount of biologically active compounds such as prostaglandins and structurally complex terpenes. (Figure ) …”

Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids

“…1 Catalytic enantioselective Nazarov cyclization is a straightforward method for introducing chiral-center-containing cyclopentenones, which are versatile chiral synthons, 2 and this strategy has attracted increasing attention in recent decades. 3 The reported asymmetric Nazarov cyclization can be roughly classified into two types on the basis of the enantioselective control step: type I Nazarov cyclization affords products with a chiral center at the β-carbon by means of an enantioselective cyclization step (Fig.…”