Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

Guillaume G. Launay; Alexandra M. Z. Slawin; David O'Hagan

doi:10.3762/bjoc.6.41

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

Guillaume G. Launay, Alexandra M. Z. Slawin, David O'Hagan

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

Abstract

The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.

Original language	English
Article number	41
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	6
DOIs	https://doi.org/10.3762/bjoc.6.41
Publication status	Published - 26 Apr 2010

Keywords

4-fluoropiperidine
4-fluoropyran
Heterocycles
Organo-fluorine
Chemistry
Prins cyclisation
Expeditious synthesis
Tetrahydropyrans
Exchange
Facile
Esters
Cope

Access to Document

10.3762/bjoc.6.41

Launay2010BeilsteinOrgChem1860 5397 6 41
© 2010 Launay et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 327 KB

Cite this

@article{d6784ffb55934e8a9b52aed2d6d5c2a2,

title = "Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles",

abstract = "The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.",

keywords = "4-fluoropiperidine, 4-fluoropyran, Heterocycles, Organo-fluorine, Chemistry, Prins cyclisation, Expeditious synthesis, Tetrahydropyrans, Exchange, Facile, Esters, Cope",

author = "Launay, {Guillaume G.} and Slawin, {Alexandra M. Z.} and David O'Hagan",

year = "2010",

month = apr,

day = "26",

doi = "10.3762/bjoc.6.41",

language = "English",

volume = "6",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Prins fluorination cyclisations

T2 - Preparation of 4-fluoro-pyran and -piperidine heterocycles

AU - Launay, Guillaume G.

AU - Slawin, Alexandra M. Z.

AU - O'Hagan, David

PY - 2010/4/26

Y1 - 2010/4/26

N2 - The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.

AB - The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.

KW - 4-fluoropiperidine

KW - 4-fluoropyran

KW - Heterocycles

KW - Organo-fluorine

KW - Chemistry

KW - Prins cyclisation

KW - Expeditious synthesis

KW - Tetrahydropyrans

KW - Exchange

KW - Facile

KW - Esters

KW - Cope

U2 - 10.3762/bjoc.6.41

DO - 10.3762/bjoc.6.41

M3 - Article

SN - 1860-5397

VL - 6

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 41

ER -

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

Abstract

Keywords

Access to Document

Fingerprint

Cite this