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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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Publisher copy:
10.1039/b808812h

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Roberts, PM More by this author
Russell, AJ More by this author
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Journal:
Organic and biomolecular chemistry
Volume:
6
Issue:
20
Pages:
3762-3770
Publication date:
2008-10-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:d6f56f3e-191e-441f-b649-a73308110543
Source identifiers:
34415
Local pid:
pubs:34415

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