Issue 11, 2011
From the journal:

Chemical Communications

Novel methodologies for the synthesis of functionalized pyroglutamates†‡

Srinivas Tekkam,a   M. A. Alam,a   Subash C. Jonnalagaddab  and  Venkatram R. Mereddy*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Minnesota Duluth, 1039 University Drive, Duluth, MN 55812, USA
E-mail: vmereddy@d.umn.edu
Fax: +1-218-726-7394
Tel: +1-218-726-6766

b Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Road, Glassboro, NJ 08028, USA
E-mail: jonnalagadda@rowan.edu
Fax: +1-856-256-4478
Tel: +1-856-256-5452

Abstract

Alkylation of amino-acid derived iminoesters with Baylis–Hillman (BH) template based allyl bromides furnished α-methylene-β-substituted-pyroglutamates, while the corresponding alkylation with BH derived allylic acetates provided α-alkylidene-pyroglutamates. These methodologies have been applied in the synthesis of fused [3.2.0]-γ-lactam-β-lactones.

Graphical abstract: Novel methodologies for the synthesis of functionalized pyroglutamates

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Article information

DOI
https://doi.org/10.1039/C0CC05609J
Article type
Communication
Submitted
16 Dec 2010
Accepted
26 Jan 2011
First published
11 Feb 2011

Chem. Commun., 2011,47, 3219-3221

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Novel methodologies for the synthesis of functionalized pyroglutamates

S. Tekkam, M. A. Alam, S. C. Jonnalagadda and V. R. Mereddy, Chem. Commun., 2011, 47, 3219 DOI: 10.1039/C0CC05609J

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