The Wieland–Miescher ketone, Hajos–Parrish–Eder–Sauer–Wiechert ketone, and their analogues are bicyclic diketones essential as building blocks for the synthesis of several natural and bioactive molecules. For this reason, since 1971, when Hajos and Parrish and Eder, Sauer, and Wiechert reported the stereoselective synthesis of these compounds promoted by L-proline, numerous methodologies and organocatalysts have been studied over the years with the aim of identifying increasingly efficient asymmetrical syntheses of these bicyclic ketones. This review will outline the methodological and stereochemical features of the organocatalytic stereoselective synthesis of these bicyclic scaffolds based on the different organocatalysts employed from 1971 until today. Particular emphasis will be given to the structural features of the catalysts and to the reaction conditions.

/pdf/organocatalyst-design-for-the-stereoselective-annulation-3isockk9.pdf

A New Chiral Synthesis of Wieland—Miescher Ketone Catalyzed by a Combination of (S)‐N‐Benzyl‐N‐(2‐pyrrolidinylmethyl)amine Derivative and Broensted Acid.

Organocatalyst Design for the Stereoselective Annulation towards Bicyclic Diketones and Analogues

Chemistry indexing and abstracting service

New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinyl-methyl)amine in the presence of dichloroacetic acid.

A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid

A New Chiral Synthesis of Wieland—Miescher Ketone Catalyzed by a Combination of (S)‐N‐Benzyl‐N‐(2‐pyrrolidinylmethyl)amine Derivative and Broensted Acid.

Citations

Organocatalyst Design for the Stereoselective Annulation towards Bicyclic Diketones and Analogues

References

A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid

Related Papers (5)

An Alternative Chiral Synthesis of Wieland—Miescher Ketone Mediated by (S)‐2‐(Pyrrolidinylmethyl)pyrrolidine: Remarkable Effects of Broensted Acid.

Asymmetric Intramolecular Aldol Reaction Mediated by (S)‐N‐Substituted‐N‐(2‐pyrrolidinylmethyl)amine to Prepare Wieland—Miescher Ketone.

Asymmetric Synthesis of Wieland—Miescher and Hajos—Parrish Ketones Catalyzed by an Amino Acid Derived Chiral Primary Amine.

Catalytic Enantioselective Crossed Aldehyde-Ketone Benzoin Cyclization.

Enantioselective Broensted Acid Catalyzed Conjugate Addition of Aryl Methyl Ketone Derived Enamines to Nitroalkenes.