Asymmetric organocatalytic heteroatomic α- and β-functionalizations of α,β-unsaturated electrophiles

ORGN 12

Martin Nielsen, kalapanka@chem.au.dk, Peter Dinér, Hao Jiang, Wei Zhuang, Søren Bertelsen, Mauro Marigo, Johanne B. Nielsen, Barbara Niess, and Karl Anker Jørgensen. Danish National Research Foundation: Center for Catalysis. Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus, Denmark
Asymmetric organocatalysis represents an important and environmentally friendly tool in the formation of stereoenriched compounds, which for many cases are of great importance for life science industry. Herein will be presented the stereoselective heteroatomic functionalization of α,β-unsaturated aldehydes and nitro olefins, e.g. the one-pot diamination of α,β-unsaturated aldehydes (Scheme 1) and the β-hydroxylation of nitro olefins (Scheme 2). Mechanistic details of the (S)-2-(bis(3,5-bis(trifluoromethyl)phenyl)(trimethylsilyloxy)methyl)pyrrolidine catalyzed β-functionalization of α,β-unsaturated aldehydes will also be presented, giving an insight into the stereoselective origin in this reaction type.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

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