Regio- and diastereocontrolled C–H insertion of chiral γ- and δ-lactam diazoacetates. Application to the asymmetric synthesis of (8S,8aS)-8-hydroxyindolizidine?

Chemical Communications Pub Date: 2006-08-02 DOI: 10.1039/B606436A

Abstract

γ- and δ-Lactam diazoacetates undergo efficient intramolecular C–H insertion catalyzed by Rh2(MPPIM)4 with excellent regioselectivity and cis-diastereoselectivity to provide synthetically useful bicyclic lactam lactones.

Graphical abstract: Regio- and diastereocontrolled C–H insertion of chiral γ- and δ-lactam diazoacetates. Application to the asymmetric synthesis of (8S,8aS)-8-hydroxyindolizidine
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