Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Autor: Cheong PH; Department of Chemistry, University of California, Berkeley, California 94720, USA., Morganelli P, Luzung MR, Houk KN, Toste FD
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2008 Apr 02; Vol. 130 (13), pp. 4517-26. Date of Electronic Publication: 2008 Mar 08.
DOI: 10.1021/ja711058f
Abstrakt: Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.
Databáze: MEDLINE