Journal article

Metal free fluoroamination of allylsilanes: A route to 3-fluoropyrrolidines

Abstract:: The intramolecular fluoroamination of homoallylic amines activated by a triisopropylsilyl or p-tolyldiisopropylsilyl group was successfully performed in the presence of Selectfluor® in acetonitrile leading to anti or syn 3-fluoropyrrolidines. The stereochemical outcome of these fluorocyclizations is dictated by the geometry of the alkene precursor. In comparison with oxygen nucleophile, the use of N-tosyl or N-Boc nucleophiles benefits from superior control over stereoselectivity but suffers from competitive fluorodesilylation. © 2012 Elsevier B.V. All rights reserved.

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APA Style

Combettes, L., Lozano, O., & Gouverneur, V. (2012). Metal free fluoroamination of allylsilanes: A route to 3-fluoropyrrolidines. Journal of Fluorine Chemistry, 143, 167–176.

MLA Style

Combettes, L, et al. “Metal Free Fluoroamination of Allylsilanes: A Route to 3-Fluoropyrrolidines.” Journal of Fluorine Chemistry, vol. 143, 2012, pp. 167–76.

Chicago Style

Combettes, L, O Lozano, and V Gouverneur. 2012. “Metal Free Fluoroamination of Allylsilanes: A Route to 3-Fluoropyrrolidines.” Journal of Fluorine Chemistry 143: 167–76.
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Publisher copy:: 10.1016/j.jfluchem.2012.05.013

Authors

+ Combettes, L More by this author

Role:: Author

+ Lozano, O More by this author

Role:: Author

+ Gouverneur, V More by this author

Role:: Author

Journal:: Journal of Fluorine Chemistry More from this journal
Volume:: 143
Pages:: 167-176
Publication date:: 2012-11-01
DOI:: 10.1016/j.jfluchem.2012.05.013
ISSN:: 0022-1139

Language:: English
Keywords:: Allylsilane

Fluorocyclization

1,2-Dipole

Selectfluor

Pyrrolidine
Pubs id:: pubs:356627
UUID:: uuid:1b9b35c4-3e51-4624-aca0-f5b6bc578d37
Local pid:: pubs:356627
Source identifiers:: 356627
Deposit date:: 2013-11-17
ARK identifier:: ark:/29072/ora_1b9b35c43e514624aca0f5b6bc578d37

Terms of use

Copyright date:: 2012

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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