New chiral camphor-based 1,4-amino alcohols as ligands for purposes of asymmetric synthesis

ORGN 77

Urvi Sheth and Vesa Nevalainen. Department of Chemistry, University of Massachusetts, 285 Old Westport Road, North Dartmouth, MA 02747
Chiral amino alcohols play an important role as chiral auxiliaries and ligands for asymmetric synthesis. Particularly 1,2-amino alcohols have been thoroughly studied whereas 1,4-analogs and higher ones have been rather poorly utilized. Converting chiral natural product, such as camphor, to chiral amino alcohols, has been an enduring research target for synthetic chemistry for decades. Recently, we described the synthesis of 1,4-amino alcohol 1 and demonstrated its utility for catalytic enantioselective synthesis. The goal of the study reported here was to synthesize and characterize 2, an analog of 1, and the related diols 3 and 4. Furthermore, a preliminary study on the utility of these novel ligands for purposes of catalytic enantioselective syntheses will be described.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004