Organocatalytic asymmetric domino reactions

ORGN 139

Henrik Sundén, henrik@organ.su.se, Ismail Ibrahem, Gui-Ling Zhao, and Armando Córdova. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, SE-10691, Sweden
Organocatalytic asymmetric domino reactions are presented. Simple chiral pyrrolidine derivatives catalyze the asymmetric domino and conjugate addition to α,β-unsaturated aldehydes with high enantioselectivity. The concept involves, first, an organocatalyzed asymmetric nucleophilic addition to the β-carbon in the iminium ion intermediate, followed by an electrophilic attack on the α-carbon in the enamine intermediate. The corresponding products are isolated in high yields and ee's.
 

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