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Stereoselective ammonium-directed epoxidation in the asymmetric syntheses of dihydroconduramines (–)-A-2, (–)-B-2, (–)-C-3 and (+)-F-3

Abstract:

Epoxidation of racemic trans -2-(N, N -dibenzylamino)cyclohex-3-en-1-ol, upon treatment with Cl 3 CCO 2 H then m -CPBA, proceeded with poor diastereoselectivity (ca. 60:40 dr), whilst epoxidation of racemic trans -2-(N -benzylamino)cyclohex-3-en-1-ol under the same conditions proceeded with high diastereoselectivity ( > 95:5 dr) and was followed by completely regioselective and stereospecific ring-opening in situ to give, after methanolysis of the intermediate trichloroacetate ester, (1 RS...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1055/s-0036-1590948

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
St Catherines College
Role:
Author
Publisher:
Thieme Publishing Publisher's website
Journal:
Synthesis Journal website
Volume:
50
Issue:
1
Pages:
64-83
Publication date:
2017-12-12
Acceptance date:
2017-10-10
DOI:
EISSN:
1437-210X
ISSN:
0039-7881
Pubs id:
pubs:813401
URN:
uri:1344c226-8528-47d1-a30e-95814fd55679
UUID:
uuid:1344c226-8528-47d1-a30e-95814fd55679
Local pid:
pubs:813401

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