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. 2014 Oct 3;16(19):5168-71.
doi: 10.1021/ol5025184. Epub 2014 Sep 17.

Origins of diastereoselectivity in Lewis acid promoted ketene-alkene [2 + 2] cycloadditions

Christopher M Rasik  1 , Young J Hong, Dean J Tantillo, M Kevin Brown
Affiliations

Origins of diastereoselectivity in Lewis acid promoted ketene-alkene [2 + 2] cycloadditions

Christopher M Rasik et al. Org Lett. .

Abstract

A detailed analysis of a Lewis acid promoted ketene-alkene [2 + 2] cycloaddition is reported. The studies have led to a rationalization for an observed inversion of diastereoselectivity between thermally induced and Lewis acid promoted ketene-alkene [2 + 2] cycloadditions. The model is supported with both experimental and computational results.

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