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Asymmetric synthesis of syn- and anti-alpha-deuterio-beta(3)-phenylalanine derivatives

Abstract:

The conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl) amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium β-amino enolates with D2O provides access to anti configured α-deuterio-β-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a range of tert-butyl α-deuterioci...

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Publication status:
Published

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
22
Issue:
10
Pages:
1035-1050
Publication date:
2011-05-31
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
Source identifiers:
179471
Language:
English
Pubs id:
pubs:179471
UUID:
uuid:4518584c-0d42-4468-86d3-b78d941685c7
Local pid:
pubs:179471
Deposit date:
2012-12-19

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