Relative stabilities of aluminum chelates of aldols involved in aldol-transfer reactions

ORGN 558

Vesa Nevalainen, vnevalainen@umassd.edu, Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747
Aldol-transfer reactions belong to the class of nucleophile-transfer reactions. These reactions are analogous to hydride-transfer reactions found by Meerwein, Pondorf, Verley, and Oppenauer. Recent experimental studies indicate that an aldol generated as a product of an aldol-transfer reaction would be more stable if it would be trapped as an aluminum chelate. The goal of the study presented in this report was to probe relative stabilities of these aluminum chelates 1 (R = aryl) and their precursors 2 using means of computational chemistry such as B3LYP/6-31G*.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

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