Taming 3-Oxetanyllithium Using Continuous Flow Technology.

Autor:	Natho P; FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari 'A. Moro', Via E. Orabona 4, 70125, Bari, Italy., Colella M; FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari 'A. Moro', Via E. Orabona 4, 70125, Bari, Italy., Andresini M; FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari 'A. Moro', Via E. Orabona 4, 70125, Bari, Italy., Degennaro L; FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari 'A. Moro', Via E. Orabona 4, 70125, Bari, Italy., Luisi R; FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari 'A. Moro', Via E. Orabona 4, 70125, Bari, Italy.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Apr 19; Vol. 26 (15), pp. 3032-3036. Date of Electronic Publication: 2024 Mar 28.
DOI:	10.1021/acs.orglett.4c00644
Abstrakt:	The oxetane ring has evolved as a useful bioisostere for dimethyl and carbonyl groups for the improvement of physiochemical properties of drug candidates. Herein, we report the generation and utilization of highly unstable 3-oxetanyllithium as a hitherto unexplored nucleophile leveraging flash technology. A range of different electrophiles are suitable reaction partners in this protocol, and we demonstrate the utility of this protocol in late-stage pharmaceutical analogue synthesis.
Databáze:	MEDLINE
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