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Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

Abstract:
Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.
Publication status:
Published

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Publisher copy:
10.1039/b509088a

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Chemical communications (Cambridge, England)
Issue:
36
Pages:
4536-4538
Publication date:
2005-09-05
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
URN:
uuid:ed79f36d-c1d0-42cf-81cb-e9810db2a2d6
Source identifiers:
110553
Local pid:
pubs:110553
Language:
English

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