Journal article

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 the two allylic positions flanking the double bond. Upon dihydroxylation, novel difluorinated cyclitol analogues were formed.

Publication status:: Published

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APA Style

Purser, S., Claridge, T., Odell, B., Moore, P., & Gouverneur, V. (2008). A two-directional approach to enantiopure 1,4-difluoro-cyclohexenes: synthesis of difluorinated cyclitol analogues. Organic Letters, 10(19), 4263–4266.

MLA Style

Purser, S, et al. “A Two-Directional Approach to Enantiopure 1,4-Difluoro-Cyclohexenes: Synthesis of Difluorinated Cyclitol Analogues.” Organic Letters, vol. 10, no. 19, 2008, pp. 4263–66.

Chicago Style

Purser, S, T Claridge, B Odell, P Moore, and V Gouverneur. 2008. “A Two-Directional Approach to Enantiopure 1,4-Difluoro-Cyclohexenes: Synthesis of Difluorinated Cyclitol Analogues.” Organic Letters 10 (19): 4263–66.
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Publisher copy:: 10.1021/ol8017402

Authors

+ Purser, S More by this author

Role:: Author

+ Claridge, T More by this author

Role:: Author

+ Odell, B More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Moore, P More by this author

Role:: Author

+ Gouverneur, V More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

Journal:: Organic letters More from this journal
Volume:: 10
Issue:: 19
Pages:: 4263-4266
Publication date:: 2008-10-01
DOI:: 10.1021/ol8017402
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Fluorine

Cyclitols

Cyclohexenes

Stereoisomerism
Pubs id:: pubs:34367
UUID:: uuid:11f15358-305d-4290-8b3e-7e3656f5e9b1
Local pid:: pubs:34367
Source identifiers:: 34367
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_11f15358305d42908b3e7e3656f5e9b1

Terms of use

Copyright date:: 2008

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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