Enantiocontrolled N-protected α-amino ketone synthesis by thiol ester—α-(thiocarbamoyl)alkylstannane cross-coupling

ORGN 133

Hao Li, hli23@emory.edu and Lanny S. Liebeskind. Department of Chemistry, Emory University, 1515 Dickey Dr, Atlanta, GA 30322
N-Protected α-amino acid thiol esters coupled with α-(thiocarbamoyl)alkylstannanes in the presence of Cu(I) thiophene-2-carboxylate (CuTC) to give high enantiopurity α-amino ketones in moderate to good yields. Using CuTC only in this alkylstannane coupling suggests a non-oxidative addition pathway. THF/Hexanes was proved to be the best solvent to inhibit the undesired S→O rearrangement.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008