Novel methodologies for the synthesis of functionalized pyroglutamates

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 t...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (11), p.3219-3221
Main Authors: Tekkam, Srinivas, Alam, M A, Jonnalagadda, Subash C, Mereddy, Venkatram R
Format: Article
Language:English
Subjects:
Alkylation
Lactones - chemistry
Pyrrolidonecarboxylic Acid - chemical synthesis
Pyrrolidonecarboxylic Acid - chemistry
Stereoisomerism
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc05609j