Organocatalysis in radical chemistry: A new method for enantioselective C-O bond formation

ORGN 107

Masayuki Hasegawa, Masayuki.Hasegawa.1@ndsu.edu and Mukund P. Sibi, Mukund.Sibi@ndsu.edu. Department of Chemistry, North Dakota State University, Ladd Hall, Fargo, ND 58105
Organocatalysis has seen limited application in radical chemistry. Herein we wish to report an efficient SET oxidation of chiral enamines with catalytic FeCl3 and application of the resulting alpha-iminium radicals in enantioselective C-O bond formation using TEMPO. The effect of the catalyst, SET reagent, solvent, and reaction conditions on the chemical efficiency and enantioselectivity will be discussed. Substrate scope and approaches to tandem bond formation will also be presented.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006