Work

Gold-Catalyzed Cycloisomerization of 1,5-Allenynes via Dual Activation of an Ene Reaction

Year: 2008

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja711058f

Authors: Paul Ha-Yeon Cheong, Philip Morganelli, Michael R. Luzung, K. N. Houk, F. Dean Toste

Institutions: University of California, Los Angeles, University of California, Berkeley

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G2679848640, Stereoselectivities of Synthetic Organic Reactions, Catalytic Methods for Carbon-Carbon and Carbon-Heteroatom Bond Formation, STEREOSELECTIVITIES IN SYNTHETIC ORGANIC REACTIONS