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Ni(II)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters

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Abstract

The enantioselective Mukaiyama–Mannich reaction of cyclic N-sulfonyl α-ketiminoesters and silyl enol ethers was realized for the first time using a Ni(II)-bis(oxazoline) complex. Both di- and tri-substituted silyl enol ethers as well as silyl dienol ethers generated from the corresponding aromatic ketones or α,β-unsaturated ketones were well tolerated in this reaction. The reaction proceeded smoothly under mild conditions to provide a series of enantioenriched benzofused sultams containing an α-quaternary α-amino ester and an aromatic ketone moiety. Moreover, the products can be readily converted into potentially bioactive benzosultams including aziridine and polycyclic benzosultams.

Graphical abstract: Ni(ii)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters

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Publication details

The article was received on 11 May 2017, accepted on 17 Jun 2017 and first published on 20 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00370F
Citation: Org. Chem. Front., 2017, Advance Article
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    Ni(II)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters

    L. Xie, H. Ma, J. Li, Y. Yu, Z. Qin and B. Fu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00370F

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