Journal
ORGANIC LETTERS
Volume 6, Issue 11, Pages 1765-1767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol049549j
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Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-beta-lactams gave enantiopure alpha-alkoxy-gamma-keto acid derivatives via a novel N1-C4 bond breakage of the beta-lactam nucleus. This is the first time that the cleavage of the N1-C4 bond on the beta-lactam nucleus has been shown to occur in 2-azetidinones lacking an aryl moiety at C4.
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