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Diastereoselective ammonium-directed epoxidation in the asymmetric syntheses of dihydroconduramines (+)-C-2, (−)-C-2, (+)-D-2, (+)-E-2, (+)-F-2, and (−)-F-2

Abstract:

Epoxidations (40% aq HBF4 then m-CPBA) of racemic cis-2-(N-benzylamino)cyclohex-3-en-1-ol and racemic cis-2-(N,N-dibenzylamino)cyclohex-3-en-1-ol proceed with very high levels of diastereoselectivity (>95:5 dr). The latter is in direct contrast to the epoxidation of the corresponding trans-diastereoisomer (which proceeds with essentially no selectivity), showing that the relative configuration of the substrate dramatically influences the diastereoselectivity in these instances. Meanwhile, ...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.8b01359

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
ORCID:
0000-0003-3181-8748
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Catherine's College
Role:
Author
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry More from this journal
Volume:
83
Issue:
17
Pages:
9939–9957
Publication date:
2018-07-24
Acceptance date:
2018-07-24
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Pmid:
30037221
Language:
English
Pubs id:
pubs:905073
UUID:
uuid:6b9a7e65-3562-46d3-aa56-1ccbfeef0518
Local pid:
pubs:905073
Source identifiers:
905073
Deposit date:
2018-08-30

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