Synthesis of substituted morpholine derivatives via In(III)-catalyzed ring-closing O-allylation

ORGN 116

Gregory R. Cook, Gregory.Cook@ndsu.edu, Jina Park, jina.park@ndsu.edu, and Ryuji Hayashi, ryuji.hayashi@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, 1231 Albrecht Avenue, P.O. Box 5516, Fargo, ND 58105-5516
Substituted morpholine derivatives are found in many compounds of pharmacological value. The efficient synthesis of novel substituted morpholine derivatives can open the door to explore new drugs. We recently reported the atom transfer cyclization catalyzed by In(III) and, importantly, we found that the reaction was driven by catalytic halide activation by under mild conditions. We have also discovered other C-C bonds formations via catalytic halide activation including ring-closing Friedel-Crafts reactions and 5-exo-trig cyclizations. We have extended this halide activation to the cynthesis of 2,6-disubstituted morpholine derivatives. Details of the diastereoselective formation of 2,6-disubstituted morpholines via In(III)-catalyzed O-allylation will be presented.

 

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

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

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