Synthesis and Structural Elucidation of 1,2‐Disubstituted 3‐Fluoropiperidines

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Title: Synthesis and Structural Elucidation of 1,2‐Disubstituted 3‐Fluoropiperidines
Authors: Fischer, PaulineMorris, MorganMüller-Bunz, HelgeEvans, Paul
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Date: 8-Mar-2020
Online since: 2020-11-30T15:36:50Z
Abstract: The work described details the reaction between Selectfluor® and a series of 1‐carbonyloxy and 1‐sulfonyl 2‐piperidines in order to generate 3‐fluoro‐2‐methoxypiperidines 3a–f. Their subsequent reaction with allyltrimethylsilane, in the presence of BF3 and TiCl4, is then reported. Studies involving a combination of single‐crystal X‐ray crystallography and NMR spectroscopy indicate that the allylation process is cis‐selective for both carbamate and sulfonamide variants and that optimal levels of diastereoselectivity are obtained using the N‐2‐nitrobenzene sulfonyl (2‐Ns) group. In this manner, the synthesis of a series of 2‐allyl 3‐fluoro‐substituted piperidines (5a, c–f) was achieved. The conversion of both the cis and trans‐N‐tosyl adducts (5d) into 3‐fluorinated analogues of the natural products pelletierine (10) and coniine (11) is subsequently detailed.
Funding Details: European Commission - European Regional Development Fund
Science Foundation Ireland
Funding Details: University of Montpellier and theErasmus+programme
Type of material: Journal Article
Publisher: Wiley
Journal: European Journal of Organic Chemistry
Volume: 2020
Issue: 9
Start page: 1165
End page: 1176
Copyright (published version): 2020 Wiley
Keywords: DiastereoselectivityElectrophilic fluorinationNatural productsNeighboring group participationSynthetic methods
DOI: 10.1002/ejoc.202000026
Language: en
Status of Item: Peer reviewed
ISSN: 1434-193X
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Appears in Collections:Chemistry Research Collection

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