Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions

Kyle F. Biegasiewicz, Michelle L. Ingalsbe, Jeffrey D. St. Denis, James L. Gleason, Junming Ho, Michelle L. Coote, G. Paul Savage, Ronny Priefer

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Recently, a novel chiral cubane-based Schiff base ligand was reported to yield modest enantioselectivity in the Henry reaction. To further explore the utility of this ligand in other asymmetric organic transformations, we evaluated its stereoselectivity in cyclopropanation and Michael addition reactions. Although there was no increase in stereocontrol, upon computational evaluation using both M06L and B3LYP calculations, it was revealed that a pseudo six-membered ring exists, through H-bonding of a cubyl hydrogen to the copper core. This decreases the steric bulk above the copper center and limits the asymmetric control with this ligand.

Original languageEnglish (US)
Pages (from-to)1814-1818
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
StatePublished - Oct 22 2012

Keywords

  • Chiral ligand
  • Cubane
  • M06L and B3LYP calculations
  • Michael addition

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions'. Together they form a unique fingerprint.

Cite this