Issue 35, 2006
From the journal:

Chemical Communications

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

Gao-jun Fan,a   Zhongyi Wanga  and  Andrew G. H. Wee*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Regina, Regina, Saskatchewan, Canada
E-mail: Andrew.Wee@uregina.ca
Fax: (1) 306-337-2409
Tel: (1) 306-585-4767

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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Article information

DOI
https://doi.org/10.1039/B606436A
Article type
Communication
Submitted
05 May 2006
Accepted
27 Jun 2006
First published
02 Aug 2006

Chem. Commun., 2006, 3732-3734

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

G. Fan, Z. Wang and A. G. H. Wee, Chem. Commun., 2006, 3732 DOI: 10.1039/B606436A

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