Substituent effects on diastereoselectivity in the microwave-assisted aza-Cope Mannich reaction

ORGN 499

Edwin L. Marrero, emarrero@emich.edu, Kathleen J. Panter, kpanter@emich.edu, and Harriet A. Lindsay, hlindsay@emich.edu. Department of Chemistry, Eastern Michigan University, 225 Mark Jefferson, Ypsilanti, MI 48197
In the course of our synthetic efforts toward the synthesis of pyrrolidine and pyrrolizidine alkaloids, we have developed a microwave-assisted version of the aza-Cope Rearrangement/Mannich cyclization for the rapid assembly of functionalized pyrrolidines. Stereochemical investigations have revealed an enhanced diastereoselectivity when bulky nitrogen protecting groups are employed (R2, Scheme). Efforts toward influencing diastereoselectivity by altering the steric demand of the protecting group and aldehyde will be presented. Additionally, the effect of microwave heating on the pyrrolidine stereoselectivity will be discussed.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

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