A practical catalytic method for preparing highly substituted cyclobutanes and cyclobutenes.

J Am Chem Soc

Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama Sendai 980-8578, Japan.

Published: March 2005

Tf2NH, an organic acid, efficiently catalyzes (2 + 2) cycloaddition reactions of silyl enol ethers with acrylates or propiolate. The process affords highly substituted cyclobutanes in high yield with high stereoselectivity under practical and environmentally benign conditions. Application for the formation of terpene skeletons and multigram synthesis of four-membered carbocycles were demonstrated.

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Source
http://dx.doi.org/10.1021/ja042661sDOI Listing

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