Novel N1−C4 β-Lactam Bond Breakage. Synthesis of Enantiopure α-Alkoxy-γ-keto Acid Derivatives

Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-β-lactams gave enantiopure α-alkoxy-γ-keto acid derivatives via a novel N1−C4 bond breakage of the β-lactam nucleus. This is the first time that the cleavage of the N1−C4 bond on the β-lactam nucleus has been shown to o...

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Bibliographic Details
Published in:Organic letters 2004-05, Vol.6 (11), p.1765-1767
Main Authors: Alcaide, Benito, Almendros, Pedro, Redondo, María C
Format: Article
Language:English
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Summary:Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-β-lactams gave enantiopure α-alkoxy-γ-keto acid derivatives via a novel N1−C4 bond breakage of the β-lactam nucleus. This is the first time that the cleavage of the N1−C4 bond on the β-lactam nucleus has been shown to occur in 2-azetidinones lacking an aryl moiety at C4.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049549j