Journal
ORGANIC LETTERS
Volume 21, Issue 1, Pages 300-304Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03745
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Funding
- Royal Society [UF140161, RG150444, RCP\EA\180031]
- EPSRC [EP/J001538/1]
- Pfizer
- Imperial College London
- European Union in the framework of the ERDF-ESF operational programme 2014-2020
- Normandy County Council
- Canceropole Nord-Ouest
- EPSRC [EP/J001538/1] Funding Source: UKRI
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Azetidines are valuable motifs that readily access under explored chemical space for drug discovery. 3,3-Diarylazetidines are prepared in high yield from N-Cbz azetidinols in a calcium(II)-catalyzed Friedel-Crafts alkylation of (hetero)aromatics and phenols, including complex phenols such as beta-estradiol. Electron poor phenols undergo O-alkylation. The product azetidines can be derivatized to drug-like compounds through the azetidine nitrogen and the aromatic groups. The N-Cbz group is crucial to reactivity by providing stabilization of an intermediate carbocation on the four-membered ring.
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