UNSPECIFIED. (2001) Palladium-catalyzed tandem reactions to form 1-vinyl-1H-isochromene derivatives. JOURNAL OF ORGANIC CHEMISTRY, 66 (10). pp. 3284-3290. ISSN 0022-3263

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Abstract

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.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
ISSN:	0022-3263
Date:	18 May 2001
Volume:	66
Number:	10
Number of Pages:	7
Page Range:	pp. 3284-3290
Identification Number:	10.1021/jo0011991
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/12136

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