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Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.

Abstract:
This article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this high diastereocontrol is also presented. The ammonium directed epoxidation methodology has been extended to more complex substrates and representative applications of this protocol in natural product synthesis are also summarised.
Publication status:
Published

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Publisher copy:
10.1039/c4ob00616j

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Publisher:
Royal Society of Chemistry
Journal:
Organic and biomolecular chemistry
Volume:
12
Issue:
26
Pages:
4544-4549
Publication date:
2014-07-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:f4b32790-246d-4651-81d0-c61c3972f0b5
Source identifiers:
466093
Local pid:
pubs:466093
Language:
English

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