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

Christopher M Rasik; Young J Hong; Dean J Tantillo; M Kevin Brown

doi:10.1021/ol5025184

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

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

Authors

Christopher M Rasik¹, Young J Hong, Dean J Tantillo, M Kevin Brown

Affiliation

¹ Indiana University , Department of Chemistry, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.

PMID: 25230201
DOI: 10.1021/ol5025184

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.