Journal article icon

Journal article

Trading N and O. Part 2: Exploiting aziridinium intermediates for the synthesis of beta-hydroxy-alpha-amino acids

Abstract:

The β-hydroxy-α-amino acids (S,S)-allo-threonine, (S,S)-β-hydroxyleucine and a range of aryl substituted (S,S)-β-hydroxyphenylalanines were prepared from the corresponding enantiopure anti-α-hydroxy-β-amino esters via a rearrangement protocol, which proceeds via the intermediacy of the corresponding aziridinium ions. The starting anti-α-hydroxy-β-amino esters were prepared in >99:1 dr using our diastereoselective aminohydroxylation procedure, whereby conjugate addition of lithium (R)-N-ben...

Expand abstract
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1016/j.tet.2014.06.057

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Roberts, PM More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
70
Issue:
35
Pages:
5849-5862
Publication date:
2014-09-02
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:df79a4b9-2b8b-4d91-a912-17524b9084bf
Source identifiers:
476787
Local pid:
pubs:476787

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