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Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines

Abstract:

We have developed a metal-free and highly diastereoselective ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes upon treatment with Cl 3CCO 2H followed by mCPBA. The reaction mechanism involves protection of the amine by protonation, hydrogen-bonded delivery of the oxidant by the allylic ammonium ion formed in situ, followed by highly regioselective ringopening of the intermediate syn-epoxide by trichloroacetic ...

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Publication status:
Published

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
Volume:
68
Issue:
12
Pages:
1295-1306
Publication date:
2010-12-01
DOI:
EISSN:
1883-6526
ISSN:
0037-9980
Source identifiers:
115850
Language:
Japanese
Keywords:
Pubs id:
pubs:115850
UUID:
uuid:9b0f5ea4-ea47-4c8d-b549-8fd305df398d
Local pid:
pubs:115850
Deposit date:
2012-12-19

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