Improved synthesis of and nucleophilic addition to 2-formyl-2-cyclohexenone

Autor:	Justin Reinicke, Gideon O. Berger, Chih-wei Chang, Klaudyna Polewacz, Hannah Seo, Phuc M. Nguyen, Elan M. Adary, Damian T. D’ Auria
Rok vydání:	2015
Předmět:	Nucleophilic addition Nucleophile Chemistry Yield (chemistry) 2-cyclohexenone Organic Chemistry Drug Discovery Michael reaction Ring (chemistry) Biochemistry Combinatorial chemistry Article Conjugate
Zdroj:	Tetrahedron Letters. 56:386-389
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.11.100
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::76aa7fdc6ae6bb1ed053ab86ecb95488 https://doi.org/10.1016/j.tetlet.2014.11.100 Zobrazit plný text záznamu Full Text from ScienceDirect