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Oxidative detagging of fluorous organosilanes

Abstract:
We have validated a novel detagging strategy featuring the unmasking of a fluorous-tagged silane to a hydroxy moiety. The fluorous silylated bicyclononane, prepared from the titanium-mediated annulation of 1-acetylcyclohexene and a fluorous-tagged allylsilane, was successfully detagged under Fleming-type oxidation conditions. The stereochemistry of the resulting hydroxylated product indicates retention of configuration upon detagging in line with the non-fluorous variant of this transformation. © 2009.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Volume:
130
Issue:
12
Pages:
1151-1156
Publication date:
2009-12-05
DOI:
ISSN:
0022-1139
URN:
uuid:239c5377-b9ff-45d6-ac59-3711e71cc421
Source identifiers:
45956
Local pid:
pubs:45956

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