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Trading N and O. Part 4: Asymmetric synthesis of syn-β-substituted-α-amino acids

Abstract:

A total of nine enantiopure syn-β-substituted-α-amino acids have been synthesised, comprising both syn-β-hydroxy-α-amino acids and syn-β-fluoro-α-amino acids. The key step in the synthetic strategy towards these syn-β-substituted-α-amino acids involves a stereospecific rearrangement, which proceeds via the intermediacy of the corresponding aziridinium ions. The requisite enantiopure syn-α-hydroxy-β-amino esters were prepared via asymmetric aminohydroxylation of the corresponding α,β-unsaturat...

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

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Publisher copy:
10.1016/j.tet.2018.04.071

Authors


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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Magdalen College
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
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Publisher:
Elsevier Publisher's website
Journal:
Tetrahedron Journal website
Volume:
74
Issue:
38
Pages:
5049-5061
Publication date:
2018-04-24
Acceptance date:
2018-04-20
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Pubs id:
pubs:847272
URN:
uri:e57dfc99-eae1-47b9-8788-5278f67af91a
UUID:
uuid:e57dfc99-eae1-47b9-8788-5278f67af91a
Local pid:
pubs:847272

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