Room temperature synthesis of highly enantio-pure α-amino ketone and peptidyl ketone by thiol ester and boronic acid cross coupling

ORGN 321

Hao Yang, hyang5@emory.edu and Lanny S. Liebeskind. Department of Chemistry, Emory University, 1515 Dickey DR NE, Atlanta, GA 30322
Enantiomerically pure α-amino ketones are extremely valuable compounds used as chiral building blocks to construct interesting bioactive molecules. A new phosphite ligand assisted Liebeskind-Srogl cross coupling reaction with high tolerance to functionality and absolute conservation of chirality was invented in our lab. Using this extremely mild reaction, α-amino thiophenyl esters or peptidyl thiophenyl esters coupled with boronic acids efficiently in the presence of catalytic Pd2dba3 and stoichiometric CuTC to give corresponding ketone products without any loss of chirality. A triethyl phosphite was introduced into this system to eradicate the decarbonylation as a side reaction.

 

New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006