Synthesis of highly substituted 2-spiropiperidines

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 wit...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-09, Vol.16 (36), p.6663-6674
Main Authors: Griggs, Samuel D, Thompson, Nathan, Tape, Daniel T, Fabre, Marie, Clarke, Paul A
Format: Article
Language:English
Subjects:
Anions
Chemical synthesis
Crystallography
Imines
Ketones
Sodium
Sodium bicarbonate
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Summary: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. Highly substituted novel 2-spiropiperidines, which are scaffolds suitable for drug discovery or natural products synthesis, were synthesized in a simple one-pot or two-pot procedure.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01272e