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Remarkable Tris(trimethylsilyl)silyl Group for Diastereoselective [2 + 2] Cyclizations

Matthew B. Boxer and Hisashi Yamamoto*

*Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email: yamamotouchicago.edu

M. B. Boxer, H. Yamamoto, Org. Lett., 2005, 7, 3127-3129.

DOI: 10.1021/ol0512334 (free Supporting Information)


Abstract

Diastereoselective [2 + 2] cyclizations of silyl enol ethers with acrylates are described. The presence of the silicon-silicon bonds of the tris(trimethylsilyl)silyl group proved to be important for this transformation. High diastereoselectivity was achieved by using the bulky bis(2,6-diphenylphenoxide) aluminum triflimide catalyst.

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proposed mechanism



Key Words

Cyclobutanols


ID: J54-Y2005-870