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Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation of Allenoates

M. N. Hopkinson, J. E. Ross, G. T. Giuffredi, A. D. Gee, V. Gouverneur* – 2010

A gold(I)-catalyzed cascade cyclization−oxidative cross-coupling process has been applied to prepare β-alkynyl-γ-butenolides directly from allenoates and various terminal alkynes. Following an initial gold-catalyzed C−O bond forming allenoate cyclization, a mechanism based on a AuI/AuIII redox cycle has been proposed with Selectfluor acting as the external oxidant.

Title
4. Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation of Allenoates
Author
M. N. Hopkinson, J. E. Ross, G. T. Giuffredi, A. D. Gee, V. Gouverneur*
Publisher
Organic Letters
Date
2010
Identifier
DOI: 10.1021/ol102061k
Source(s)
Citation
Org. Lett. 2010, 12, 4904-4907