70147-63-6Relevant articles and documents
Expeditious copper-catalyzed conjugate 1,4-addition of bromo[2-(1,3-dioxolan-2-yl)ethyl]magnesium to α,β-cycloalkenones and subsequent transformations
Tsantali, Georgia G.,Takakis, Ioannis M.
, p. 6455 - 6458 (2003)
Expeditious CuI-catalyzed conjugate 1,4-addition of bromo [2-(1,3-dioxolan-2-yl)ethyl] magnesium to the five-, six-, seven-, and eight-membered α,β-cycloalkenones is described. The reaction times are decreased dramatically compared to CuBr-(CH3
Cyclopentene and Cyclohexene Annulation via Copper-Catalyzed Conjugate Addition of Acetal-Containing Grignard Reagents
Bal, Swati A.,Marfat, Anthony,Helquist, Paul
, p. 5045 - 5050 (2007/10/02)
The Grignard reagents 2 derived from 2-(bromoethyl)- and 2-(3-chloropropyl)-1,3-dioxolane undergo conjugate addition to a number of α,β-unstaurated ketones in the presence of a catalytic amount of a cuprous salt.The resulting keto acetals, upon treatment with hydrochloric acid, undergo sequential hydrolysis, intramolecular aldol condensation, and dehydration to give cyclopentene and cyclohexene annulation products.The entire series of reactions, starting with the conjugate addition, may be performed as a one flask experiment leading to direct formation of thecyclization products.The Grignard reagents may also be alkylated with epoxides or acylated with an acid chloride to give intermediates that may be converted into cyclic products by pathways related to those above.
