Cyclopropane fragmentation approaches to the synthesis of piperidines and azepines

ORGN 136

Marita C. Lawler, lawle2mc@jmu.edu, Alison M. Whitehurst, whiteham@jmu.edu, and Kevin P. C. Minbiole, minbiokp@jmu.edu. Department of Chemistry and Biochemistry, James Madison University, MSC 4501, Harrisonburg, VA 22807
The ring expansion of hydroxycylopropanes can be exploited for the stereocontrolled formation of oxygenated heterocycles such as oxepanes. Progress has been made toward the synthesis of nitrogenous heterocycles, particularly piperidines and azepines, via analogous fragmentation/recondensation strategies. This method attempts to condense carbamate-substituted cyclopropyl alcohols with an aldehyde or acetal, producing an aminal. Under Lewis acid promotion, the aminal is expected to rearrange to form a piperidine or azepine. This rearrangement is still under investigation and has shown limited success.

 

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

Division of Organic Chemistry

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