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Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones.

ABSTRACT: The enantioselective cross aldol reaction of 1-benzyl 4,5-dioxo-2-aryl-4,5-dihydro-1H-pyrrole-3-carboxylates and ketones was studied with proline derivatives or cinchona alkaloid-derived primary amines as the catalysts for the first time. trans-4-Benzoyloxy-L-proline (15) was found to be the best catalyst for acyclic ketones. For cyclohexanone, the best results were achieved with 9-deoxy-9-epi-aminoquinine (18) as the catalyst in the presence of racemic 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (19) as the cocatalyst. Using these protocols, 3-alkyl-3-hydroxy-1H-pyrrol-2(3H)-one derivatives were obtained in excellent yields and good to high ee values (up to 94% ee).

SUBMITTER: Bhanushali M

PROVIDER: S-EPMC3335438 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones.

Bhanushali Mayur M Zhao Cong-Gui CG

Tetrahedron letters 20111119 3

The enantioselective cross aldol reaction of 1-benzyl 4,5-dioxo-2-aryl-4,5-dihydro-1H-pyrrole-3-carboxylates and ketones was studied with proline derivatives or cinchona alkaloid-derived primary amines as the catalysts for the first time. trans-4-Benzoyloxy-L-proline (15) was found to be the best catalyst for acyclic ketones. For cyclohexanone, the best results were achieved with 9-deoxy-9-epi-aminoquinine (18) as the catalyst in the presence of racemic 1,1'-binaphthyl-2,2'-diyl hydrogen phospha ...[more]

PMID: 22544980

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