title: 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.
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Elan M
authors.initials: EM
authors.lastname: Adary
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Chang
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Damian T D'
authors.initials: DT
authors.lastname: Auria
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Phuc M
authors.initials: PM
authors.lastname: Nguyen
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Klaudyna
authors.initials: K
authors.lastname: Polewacz
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Justin A
authors.initials: JA
authors.lastname: Reinicke
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Hannah
authors.initials: H
authors.lastname: Seo
authors.affiliation: Department of Natural Sciences, Hawai'i Pacific University, Honolulu, Hawai'i, 96813.
authors.forename: Gideon O
authors.initials: GO
authors.lastname: Berger
keywords: 2-formyl-2-cycloalkenone; 2-formyl-2-cyclohexenone; Michael Addition; conjugate addition; dimethylmalonate