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Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation

Abstract:
A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1021/acs.orglett.6b02959

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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Grant:
People Programme (Marie Curie Actions) of the European Union’s Seventh Framework Programme (FP7/2007-2013)
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Grant:
Award No. 2014/16516-9
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
18
Issue:
22
Pages:
5880–5883
Publication date:
2016-11-09
Acceptance date:
2016-11-08
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pubs id:
pubs:659142
URN:
uri:b6d91f88-576d-4f83-85ba-e62b0f503d06
UUID:
uuid:b6d91f88-576d-4f83-85ba-e62b0f503d06
Local pid:
pubs:659142
Paper number:
22

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