347392-10-3Relevant academic research and scientific papers
Enantioselective synthesis of 2,3-disubstituted indanones via Pd-catalyzed intramolecular asymmetric allylic alkylation of ketones
Li, Xiao-Hui,Zheng, Bao-Hui,Ding, Chang-Hua,Hou, Xue-Long
supporting information, p. 6086 - 6089 (2014/01/06)
A Pd-catalyzed intramolecular asymmetric allylic alkylation (AAA) reaction with "hard" carbanions has been developed for the first time, affording 2,3-disubstituted indanones with high diastereo- and enantioselectivities. The transformation of these produ
Palladium-catalyzed tandem reactions to form 1-vinyl-1H-isochromene derivatives
Mutter,Campbell,de la Nava,Merritt,Wills
, p. 3284 - 3290 (2007/10/03)
The palladium-catalyzed reaction of pinacolone with tert-butyldimethyl(3-(2-bromophenyl)allyloxy)-silane results in direct formation of 1-vinyl-3-tert-butyl-1H-isochromene. This is the result of a ketone arylation followed by an intramolecular cyclization of the enolate with the allylic system. The use of a lithium diamide base appears to be essential for success. The tert-butyldimethylsilyl protecting group is also an essential choice as it furnishes the appropriate reactivity to promote allylic substitution after the aryl coupling process. The use of more effective leaving groups, such as acetate, results in reaction of the allylic group, and no aryl coupling is observed. Through the appropriate selection of phosphine ligand and solvent, either the cyclized isochromene product or the noncyclized intermediate may be formed selectively. A short combinatorial study of the scope and limitations of the reaction, involving 24 ketones, is described.
