The azomethine ylide strategy for β-lactam synthesis. Azapenams and 1-azacephams

D Brown, GA Brown, M Andrews, JM Large…

Index: Brown, David; Brown, Giles A.; Andrews, Mark; Large, Jonathan M.; Urban, Dominique; Butts, Craig P.; Hales, Neil J.; Gallagher, Timothy Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 17 p. 2014 - 2021

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Citation Number: 22

Abstract

Reaction of the β-lactam-based oxazolidinone 5 with N-sulfonylimines provides the exo and endo azapenams 8 in 22–54% yield. The reactivity of 2H-azirines as 1, 3-dipolarophiles towards β-lactam-based azomethine ylides derived from oxazolidinones 5 and 15 has also been evaluated. Azirines 11 and 12a provide cycloadducts 13a, b and 16 respectively, which incorporate the novel 2, 6-diazatricyclo [4.2. 0.02, 4] octan-7-one ring system. These ...