Journal article

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.

Abstract:: The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Publication status:: Published

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APA Style

Aciro, C., Davies, S., Roberts, P., Russell, A., Smith, A., & Thomson, J. (2008). Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol. Organic and Biomolecular Chemistry, 6(20), 3762–3770.

MLA Style

Aciro, C, et al. “Ammonium-Directed Dihydroxylation: Metal-Free Synthesis of the Diastereoisomers of 3-Aminocyclohexane-1,2-Diol.” Organic and Biomolecular Chemistry, vol. 6, no. 20, 2008, pp. 3762–70.

Chicago Style

Aciro, C, S Davies, P Roberts, A Russell, A Smith, and J Thomson. 2008. “Ammonium-Directed Dihydroxylation: Metal-Free Synthesis of the Diastereoisomers of 3-Aminocyclohexane-1,2-Diol.” Organic and Biomolecular Chemistry 6 (20): 3762–70.
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Publisher copy:: 10.1039/b808812h

Authors

+ Aciro, C More by this author

Role:: Author

+ Davies, S More by this author

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

+ Roberts, P More by this author

Role:: Author

+ Russell, A More by this author

Role:: Author

+ Smith, A More by this author

Role:: Author

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Journal:: Organic and biomolecular chemistry More from this journal
Volume:: 6
Issue:: 20
Pages:: 3762-3770
Publication date:: 2008-10-01
DOI:: 10.1039/b808812h
EISSN:: 1477-0539
ISSN:: 1477-0520

Language:: English
Keywords:: Cyclohexanols

Substrate Specificity

Oxidation-Reduction

Cyclohexylamines

Hydroxylation

Hydroxides

Metals

Quaternary Ammonium Compounds

Stereoisomerism
Pubs id:: pubs:34415
UUID:: uuid:d6f56f3e-191e-441f-b649-a73308110543
Local pid:: pubs:34415
Source identifiers:: 34415
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_d6f56f3e191e441fb649a73308110543

Terms of use

Copyright date:: 2008

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

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