Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams
- PMID: 20707384
- DOI: 10.1021/jo101004x
Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: synthesis of functionalized chiral γ-lactams
Abstract
A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral γ-lactams in a domino fashion has been developed. γ-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.
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