Enantioselective synthesis of disubstituted cyclopentenes by N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones

ORGN 388

Manabu Wadamoto, m-wadamoto@northwestern.edu and Karl A. Scheidt, scheidt@northwestern.edu. Department of Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208
The desymmetrization of achiral molecules is powerful strategy for the synthesis of optically active materials. The conversion of simple precursors into functionalized products is a continuing goal in chemistry to efficiently access complex architectures for use in total synthesis and medicinal chemistry. An especially challenging stereogenic motif in organic chemistry is a quaternary carbon center. Chiral N-heterocyclic carbenes (NHCs) are highly selective catalysts for the intramolecular aldol reaction of the 1,3-diketones to afford optically active cyclopentene compounds after decarboxylation of bicyclic lactone intermediates. The scope and details of the reaction will be presented.