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

Org Lett

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

Published: October 2014

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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http://dx.doi.org/10.1021/ol5025184DOI Listing

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