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Trading N and O: asymmetric syntheses of beta-hydroxy-alpha-amino acids via alpha-hydroxy-beta-amino esters

Abstract:

Both diastereoisomers of 2-amino-3-hydroxybutanoic acid and 2-amino-3-hydroxy-3-phenylpropanoic acid have been prepared from enantiopure α-hydroxy-β-amino esters via the intermediacy of the corresponding cis- and trans-aziridines. Aminohydroxylation of two α,β-unsaturated esters produced enantiopure 2,3-anti-α-hydroxy-β-amino esters in >99:1 dr. Subsequent epimerisation at the C(2)-position via a sequential oxidation/diastereoselective reduction protocol gave the corresponding enantiopure ...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2013.08.007

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Roberts, PM More by this author
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Journal:
TETRAHEDRON
Volume:
69
Issue:
42
Pages:
8885-8898
Publication date:
2013-10-21
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:61f46d6a-68b8-46c2-afa8-176d7132061a
Source identifiers:
418955
Local pid:
pubs:418955

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