- 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...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/ol8017402
-
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- 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:
- Copyright date:
- 2008
Journal article
A two-directional approach to enantiopure 1,4-difluoro-cyclohexenes: synthesis of difluorinated cyclitol analogues.
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