Synthesis 2010(1): 98-102  
DOI: 10.1055/s-0029-1217083
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Novel Chiral Cubane-Based Schiff Base Ligand and Its Application in Asymmetric Nitro-Aldol (Henry) Reactions

Michelle L. Ingalsbea, Jeffrey D. St. Denisb, James L. Gleasonb, G. Paul Savagec, Ronny Priefer*a
a Department of Chemistry, Biochemistry, and Physics, Niagara University, Niagara, NY 14109, USA
Fax: +1(716)2868254; e-Mail: rpriefer@niagara.edu;
b Department of Chemistry, McGill University, Montreal, QC, H3A 2K6, Canada
c CSIRO Molecular and Health Technologies, Clayton South MDC 3169, Australia
Further Information

Publication History

Received 16 July 2009
Publication Date:
22 October 2009 (online)

Abstract

The first reported cubane-based chiral Schiff base ligand has been successfully synthesized. This ligand has been evaluated on the nitro-aldol (Henry) reaction. The reactions were performed in the presence of four different copper salts, using eight different solvents, and five different temperatures. The highest enantioselectivity obtained for this novel ligand was ˜39% ee.