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Improved Synthesis of and Nucleophilic Addition to 2-Formyl-2-Cyclohexenone.

ABSTRACT: A preparation of 2-formyl-2-cyclohexenone in nearly quantitative yield and purity of approximately 95% is described. It is scalable and has been extended to the synthesis of the 5- and 7-membered ring homologs with comparable yields. Conditions have also been developed for the successful conjugate addition of dimethylmalonate to 2-formyl-2-cyclohexenone, in good and scalable yield (60%). This result has been extended to 5 other nucleophile classes, and the dimethylmalonate conjugate addition has been demonstrated with 2-formyl-2-cyclopentenone and 2-formyl-2-cycloheptenone.

SUBMITTER: Adary EM

PROVIDER: S-EPMC4290381 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Improved Synthesis of and Nucleophilic Addition to 2-Formyl-2-Cyclohexenone.

Adary Elan M EM Chang Chih-Wei CW Auria Damian T D' DT Nguyen Phuc M PM Polewacz Klaudyna K Reinicke Justin A JA Seo Hannah H Berger Gideon O GO

Tetrahedron letters 20150101 2

A preparation of 2-formyl-2-cyclohexenone in nearly quantitative yield and purity of approximately 95% is described. It is scalable and has been extended to the synthesis of the 5- and 7-membered ring homologs with comparable yields. Conditions have also been developed for the successful conjugate addition of dimethylmalonate to 2-formyl-2-cyclohexenone, in good and scalable yield (60%). This result has been extended to 5 other nucleophile classes, and the dimethylmalonate conjugate addition has ...[more]

PMID: 25593375

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