Issue 4, 2012

Valine sulfonamidecinnamic acid asymmetric crystal reactions

Abstract

Racemic and homochiral valine sulfonamidecinnamic acids crystallize with components aligned by use of the complementary features of hydrogen bonds and molecular topology to give supramolecular dimers. These discrete motifs effectively organize adjacent olefins for UV initiated single-crystal-to-single-crystal [2+2] photodimerization reactions. The racemic crystals produce inversion related cyclobutane products, while the desymmetrized crystalline architectures of the homochiral phase promote asymmetric photodimerization with 90% conversion.

Graphical abstract: Valine sulfonamidecinnamic acid asymmetric crystal reactions

Supplementary files

Article information

Article type
Communication
Submitted
15 Aug 2011
Accepted
08 Nov 2011
First published
25 Nov 2011

Chem. Commun., 2012,48, 519-521

Valine sulfonamidecinnamic acid asymmetric crystal reactions

K. A. Wheeler, S. H. Malehorn and A. E. Egan, Chem. Commun., 2012, 48, 519 DOI: 10.1039/C1CC15068E

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