Journal article icon

Journal article

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 ...

Expand abstract
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1016/j.tet.2013.08.007

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Expand authors...
Journal:
TETRAHEDRON
Volume:
69
Issue:
42
Pages:
8885-8898
Publication date:
2013-10-21
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Source identifiers:
418955
Language:
English
Keywords:
Pubs id:
pubs:418955
UUID:
uuid:61f46d6a-68b8-46c2-afa8-176d7132061a
Local pid:
pubs:418955
Deposit date:
2013-11-16

Terms of use


Views and Downloads






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

TO TOP