Enantiodifferentiating photoisomerization of (Z,Z)-1,3-cyclooctadiene included and sensitized by naphthoyl-curdlan

Gaku Fukuhara; Mami Imai; Cheng Yang; Tadashi Mori; Yoshihisa Inoue

doi:10.1021/ol2003644

Enantiodifferentiating photoisomerization of (Z,Z)-1,3-cyclooctadiene included and sensitized by naphthoyl-curdlan

Org Lett. 2011 Apr 1;13(7):1856-9. doi: 10.1021/ol2003644. Epub 2011 Mar 1.

Authors

Gaku Fukuhara¹, Mami Imai, Cheng Yang, Tadashi Mori, Yoshihisa Inoue

Affiliation

¹ Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp

PMID: 21361291
DOI: 10.1021/ol2003644

Abstract

6-O-(2-naphthoyl)curdlan was newly synthesized as a sensitizing polysaccharide host to examine the chiroptical properties, supramolecular complexation, and photochirogenic behavior with (Z,Z)-1,3-cyclooctadiene (1ZZ). The enantiodifferentiating photoisomerization of 1ZZ included and sensitized by this polysaccharide host gave a highly strained chiral (E,Z)-isomer in up to 8.7% enantiomeric excess (ee) in solution and 11.7% ee in the solid state, which are the highest values ever reported for a supramolecular photochirogenesis of 1EZ.