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Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate.

Abstract:
A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.
Publication status:
Published

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Publisher copy:
10.1039/b408257e

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Chemical Communications
Volume:
10
Issue:
21
Pages:
2502-2503
Publication date:
2004-11-01
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
Source identifiers:
110545
Language:
English
Keywords:
Pubs id:
pubs:110545
UUID:
uuid:05605471-12ef-4669-b20c-57714d02c787
Local pid:
pubs:110545
Deposit date:
2012-12-19

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