Strategy for preparing enantiomerically pure SNF analogs with chiral auxiliary

ORGN 756

Kathlyn A. Parker, and Keunsoo Kim, Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400
While we investigate chiral auxiliaries in 8π (8π, 6π) electrocyclization for preparing enantiomerically pure SNF analogues, we initially obtained two endo diastereomeric products with low diastereoselectivity. And, separation of diastereomeric products was challenging. Recently, we found a model system which can be easily separated on chromatography. In addition, new auxiliaries for this asymmetric 8π electrocyclization are under active investigation. This approach could allow to prepare enantiomerically pure natural products containing bicyclo[4.2.0]-2,4-octadiene core as well as SNF analogues.