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Synthesis of highly substituted 2-spiropiperidines

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JournalOrganic and Biomolecular Chemistry
DateAccepted/In press - 19 Jul 2018
DateE-pub ahead of print - 30 Jul 2018
DatePublished (current) - 19 Sep 2018
Issue number36
Volume16
Number of pages12
Pages (from-to)6663-6674
Early online date30/07/18
Original languageEnglish

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.

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© The Royal Society of Chemistry 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

    Research areas

  • 2-spiropiperidines, medicinal chemistry

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