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Issue 8, 2016
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One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties

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Abstract

We successfully expand the application of lactols or cyclic hemiaminals as nucleophiles for the asymmetric synthesis of both N,O- and N,N-acetal moieties contained in the structure of ring-fused piperidine derivatives. This efficient one-pot protocol involves an organocatalyzed asymmetric aza-Diels–Alder reaction and iminium ion induced cyclization sequence to ultimately deliver heterocyclic compounds with excellent stereoselectivity in high yield, containing three continuous stereogenic centers.

Graphical abstract: One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties

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Publication details

The article was received on 15 Dec 2015, accepted on 15 Jan 2016 and first published on 19 Jan 2016


Article type: Paper
DOI: 10.1039/C5OB02571K
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Citation: Org. Biomol. Chem., 2016,14, 2444-2453
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    One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties

    J. Li, Z. Li, W. Zhao, Y. Liu, Z. Tong and R. Tan, Org. Biomol. Chem., 2016, 14, 2444
    DOI: 10.1039/C5OB02571K

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