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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 ...

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Journal:
Journal of Fluorine Chemistry
Volume:
143
Pages:
167-176
Publication date:
2012-11-05
DOI:
ISSN:
0022-1139
URN:
uuid:1b9b35c4-3e51-4624-aca0-f5b6bc578d37
Source identifiers:
356627
Local pid:
pubs:356627

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