Controlled diastereoselectivity at the alkene-geometry through selective encapsulation: E-Z photoisomerization of oxazolidinone-functionalized enecarbamates within hydrophobic nano-cavities

Hideaki Saito; J Sivaguru; Steffen Jockusch; Joanne Dyer; Yoshihisa Inoue; Waldemar Adam; Nicholas J Turro

doi:10.1039/b609177f

Controlled diastereoselectivity at the alkene-geometry through selective encapsulation: E-Z photoisomerization of oxazolidinone-functionalized enecarbamates within hydrophobic nano-cavities

Chem Commun (Camb). 2007 Feb 28:(8):819-21. doi: 10.1039/b609177f. Epub 2006 Nov 14.

Authors

Hideaki Saito¹, J Sivaguru, Steffen Jockusch, Joanne Dyer, Yoshihisa Inoue, Waldemar Adam, Nicholas J Turro

Affiliation

¹ Department of Chemistry, Columbia University, 3000 Broadway, Mail Code 3119, New York, NY 10027, USA.

PMID: 17308642
DOI: 10.1039/b609177f

Abstract

Photoisomerization of encapsulated Z-enecarbamates within the hydrophobic chiral cavities of gamma-CD showed higher diastereoselectivities in the photoproducts than those obtained in solution. The selective encapsulation of the enecarbamates and the following isomerization process are both diastereoselectively controlled by gamma-CD.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkenes / chemistry*
Carbamates / chemistry*
Circular Dichroism
Indicators and Reagents
Isomerism
Magnetic Resonance Spectroscopy
Oxazolidinones / chemistry*
Photochemistry
Solutions
Stereoisomerism

Substances

Alkenes
Carbamates
Indicators and Reagents
Oxazolidinones
Solutions