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Allylic-Allylic Alkylation with 3,5-Dimethyl-4-nitroisoxazole: A Route to Dicarboxylic Acid Derivatives.

ABSTRACT: In this work, the first application of 3,5-dimethyl-4-nitroisoxazole as a vinylogous pronucleophile in the allylic-allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been realized under nucleophilic catalysis conditions with dimeric cinchona alkaloids, providing excellent enantiocontrol of the process. The usefulness of the products thus obtained has been confirmed in selected chemoselective reactions. The most important one involves the transformation of the isoxazole moiety into a carboxylic acid group, thus opening access to dicarboxylic acid derivatives.

SUBMITTER: Kowalczyk-Dworak D

PROVIDER: S-EPMC7497636 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Allylic-Allylic Alkylation with 3,5-Dimethyl-4-nitroisoxazole: A Route to Dicarboxylic Acid Derivatives.

Kowalczyk-Dworak Dorota D Kwit Marcin M Albrecht Łukasz Ł

The Journal of organic chemistry 20200220 5

In this work, the first application of 3,5-dimethyl-4-nitroisoxazole as a vinylogous pronucleophile in the allylic-allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been realized under nucleophilic catalysis conditions with dimeric cinchona alkaloids, providing excellent enantiocontrol of the process. The usefulness of the products thus obtained has been confirmed in selected chemoselective reactions. The most important one involves the transformation of ...[more]

PMID: 32040920

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