Chiral anthracene derivatives as facially restrictive chiral auxiliaries

ORGN 385

Xiang Liu, liuxiang@chem.bu.edu, Department of Chemistry, Boston University, 590 commonwealth Ave, Boston, MA 02215 and John K. Snyder, jsnyder@bu.edu, Chemistry Department, Boston University, 590 commonwealth Ave, Boston, MA 02215.
New stereocontrolling auxiliaries have been designed based on a facially restrictive pyrrolidone motif that can be used in a variety of highly stereoselective synthetic transformations. These chiral auxiliaries (1 and 2), easily prepared from a completely enantioselective Diels-Alder reaction between a chiral anthracene and maleimide followed by a regioselective reduction of one carbonyl group, have been successfully applied to highly diastereoselective Diels-Alder cycloadditions, conjugate additions, and aldol reactions with high yields (Scheme 1). This auxiliary also provides excellent "cleavability" with complete auxiliary recovery, which in the auxiliary removal process allows for the production of diversified derivatives.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Tuesday, August 21, 2007 BCEC -- 253C, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007