Related Experiment Videos
Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals
1Graduate School of Pharmaceutical Sciences, University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Organic Letters
|June 29, 2001
Abstract:
[figure: see text] Ring-opening reactions of semicyclic N,O-acetals with various nucleophiles such as silyl enol ethers are effectively catalyzed by a Lewis acid (TMSOTf). Reactions of 3-substituted N,O-acetals showed high diastereoselectivities. Synthetic utility of this method has been demonstrated in the stereoselective synthesis of an anti-malarial agent, isofebrifugine.