Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams

Ghorai, Manas K. ; Tiwari, Deo Prakash (2010) Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams The Journal of Organic Chemistry, 75 (18). pp. 6173-6181. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo101004x

Related URL: http://dx.doi.org/10.1021/jo101004x

Abstract

A highly enantio- and diastereoselective Lewis acid catalyzed SN2-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.

Item Type:Article
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ID Code:117121
Deposited On:15 Apr 2021 08:01
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