Journal article icon

Journal article

Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate: A practical method for the C-alpha epimerization of anti beta-amino-alpha-hydroxy acids

Abstract:
A practical method to convert anti β-amino-α-hydroxy acids into the corresponding syn esters via the DCC/DMAP-HCl mediated esterification was devised, and methyl (2R,3S)-(E)-3-t-butoxycarbonylamino-2-hydroxy-4-hexenoate 15 was synthesised from the corresponding (2S,3S)-isomer 9 using the epimerization procedure developed. The α- and β-stereogenic centres of 9 were constructed by the Michael addition of a homochiral lithium amide to t- butyl sorbate and subsequent oxidation of the enolate intermediate in one pot.
Publication status:
Published

Actions


Access Document


Authors


Brackenridge, I More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fenwick, DR More by this author
Ichihara, O More by this author
Polywka, MEC More by this author
Journal:
TETRAHEDRON
Volume:
55
Issue:
2
Pages:
533-540
Publication date:
1999-01-08
DOI:
ISSN:
0040-4020
URN:
uuid:5b3cac50-5033-40dd-9ba9-35e458a80147
Source identifiers:
110622
Local pid:
pubs:110622
Language:
English

Terms of use


Metrics



If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP