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A two-directional approach to enantiopure 1,4-difluoro-cyclohexenes: synthesis of difluorinated cyclitol analogues.

Abstract:

Enantiopure 1,4-difluoro-cyclohexenes were prepared from readily available acetonide-protected (3 S,4 S)-hexa-1,5-diene-3,4-diol. In a two-directional mode, a double cross-metathesis reaction using allyltrimethylsilane as the olefinic partner, followed by electrophilic fluorination, afforded diastereomeric acetonide-protected 3,6-difluoro-octa-1,7-diene-4,5-diols. These dienes were found to be suitable substrates for ring-closing metathesis, delivering cyclohexenes featuring fluorine atoms on...

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Publication status:
Published

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Publisher copy:
10.1021/ol8017402

Authors


Claridge, TD More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
10
Issue:
19
Pages:
4263-4266
Publication date:
2008-10-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:11f15358-305d-4290-8b3e-7e3656f5e9b1
Source identifiers:
34367
Local pid:
pubs:34367
Language:
English
Keywords:

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