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Lewis Acid-Catalyzed Ring-Opening Reactions of Semicyclic N , O -Acetals

2001; American Chemical Society; Volume: 3; Issue: 3 Linguagem: Inglês

10.1021/ol006990a

1523-7060

Masaharu Sugiura, Shū Kobayashi,

Asymmetric Synthesis and Catalysis

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.