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

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Matthew B. Boxer and Hisashi Yamamoto*

Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637

Org. Lett., 2005, 7 (14), pp 3127–3129

DOI: 10.1021/ol0512334

Publication Date (Web): June 8, 2005

Section:

Alicyclic Compounds

Abstract

Diastereoselective [2 + 2] cyclizations of aldehyde- and ketone-derived silyl enol ethers with acrylates is described. The use of the tris(trimethylsilyl)silyl group allows for unprecedented reactivity, yields, and selectivity for these cyclizations. The presence of silicon−silicon bonds proved to be important for this transformation, where typical silyl groups (TBS and TIPS) failed to give any desired product. The bulky bis(2,6-diphenylphenoxide) aluminum triflimide catalyst was essential for high diastereoselectivity.

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

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