Gold-catalyzed three-component tandem process: an efficient and facile assembly of complex butenolides from alkynes, amines, and glyoxylic acid.

An efficient and facile gold-catalyzed three-component tandem process for the assembly of two types of highly functionalized butenolides has been developed. In this reaction system, more than four chemical bonds are formed by a single gold catalyst. The present tandem protocol includes a direct coupling of alkynes, amines, and glyoxylic acid and subsequent exclusively endo-selective cycloisomerization of alkynoic acids along with intermolecular electrophilic trapping; it utilizes three simple and commercially available starting materials to assemble architecturally complex and appealing butenolide scaffolds bearing other reactive sites for further manipulation.

Citation

Qiang Zhang, Ming Cheng, Xiaoyu Hu, Bo-Gang Li, Jian-Xin Ji. Gold-catalyzed three-component tandem process: an efficient and facile assembly of complex butenolides from alkynes, amines, and glyoxylic acid. Journal of the American Chemical Society. 2010 Jun 2;132(21):7256-7

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PMID: 20455531

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