Enantioselective recognition of chiral atropisomeric N-arylimides

ORGN 418

Brooke N. Bullock, bullocbn@mailbox.sc.edu1, Roger Rasberry, rasberry@mail.chem.sc.edu2, and Ken D. Shimizu, shimizu@mail.chem.sc.edu2. (1) Department of Chemistry & Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, (2) Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208
Axially chiral atropisomers such as BINOL and BINAP are important and highly effective chiral ligands, catalysts, and resolving agents. The difficulty in exploring this class of chiral molecules is that their syntheses are difficult due to the necessity of forming a highly hindered Csp-Csp bond. We have been exploring the enantioselective recognition properties of a readily accessible class of axially chiral atropisomers based on the hindered rotation about the Caryl-Nimide bond. These can be easily prepared in high yields via condensation of an unsymmetrical cyclic anhydride and an ortho substituted aniline. The resolution and study of their enantioselective recognition properties will be reported.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008