Diastereospecific fluorination of substituted azepanes

Alpesh Ramanlal Patel; Fei Liu

doi:10.1016/j.tet.2012.10.078

Diastereospecific fluorination of substituted azepanes

Alpesh Ramanlal Patel, Fei Liu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

Fluorination of bioactive compounds is an important step in drug discovery and development. Fluorination has been extensively studied in acyclic systems, carbocycles, and fused heterocycles. However, there is no report on fluorination of azepanes. As azepanes are components of many biologically active substances and natural products. We herein present the first fluorination examples of substituted azepanes. Fluoroazepanes were prepared by deoxyfluorination diastereospecifically in excellent yields. The absolute configuration at the fluorination site was unambiguously assigned by 2D NMR spectroscopy.

Original language	English
Pages (from-to)	744-752
Number of pages	9
Journal	Tetrahedron
Volume	69
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2012.10.078
Publication status	Published - 14 Jan 2013

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10.1016/j.tet.2012.10.078

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AB - Fluorination of bioactive compounds is an important step in drug discovery and development. Fluorination has been extensively studied in acyclic systems, carbocycles, and fused heterocycles. However, there is no report on fluorination of azepanes. As azepanes are components of many biologically active substances and natural products. We herein present the first fluorination examples of substituted azepanes. Fluoroazepanes were prepared by deoxyfluorination diastereospecifically in excellent yields. The absolute configuration at the fluorination site was unambiguously assigned by 2D NMR spectroscopy.

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Diastereospecific fluorination of substituted azepanes

Abstract

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