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Synthesis of highly substituted 2-spiropiperidines

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Abstract

2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland–Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.

Graphical abstract: Synthesis of highly substituted 2-spiropiperidines

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Publication details

The article was received on 29 May 2018, accepted on 19 Jul 2018 and first published on 30 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01272E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of highly substituted 2-spiropiperidines

    S. D. Griggs, N. Thompson, D. T. Tape, M. Fabre and P. A. Clarke, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01272E

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