1376710-73-4Relevant articles and documents
Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones
Lee, Jeonghyo,Wang, Sibin,Callahan, Miranda,Nagorny, Pavel
supporting information, p. 2067 - 2070 (2018/04/16)
This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.
Vinyl Weinreb amides: A versatile alternative to vinyl ketone substrates for the Heck arylation
Baker, David B.,Gallagher, Peter T.,Donohoe, Timothy J.
, p. 3690 - 3697 (2013/05/08)
This paper describes the use of unsaturated Weinreb amides as excellent substrates for the Heck reaction. Subsequent derivatization of the products with organometallic reagents allowed access to a variety of substituted vinyl ketones that could not have been prepared directly via Heck reaction on unsaturated ketone precursors.
