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Asymmetric synthesis of (-)-(R)-sitagliptin

Abstract:

The asymmetric synthesis of (-)-(R)-sitagliptin was achieved in seven steps from commercially available starting materials using the highly diastereoselective conjugate additions of either lithium (R)-N-benzyl-N- (α-methylbenzyl)amide or lithium (R)-N-benzyl-N-(α-methyl-p- methoxybenzyl)amide to tert-butyl 4-(2′,4′,5′-trifluorophenyl) but-2-enoate to install the correct stereochemistry. Subsequent sequential acid-catalysed hydrolysis of the resultant β-amino esters, HOBt/EDC mediated coupling...

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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
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
53
Issue:
24
Pages:
3052-3055
Publication date:
2012-06-13
DOI:
EISSN:
1873-3581
ISSN:
0040-4039
Source identifiers:
331934
Language:
English
Keywords:
Pubs id:
pubs:331934
UUID:
uuid:b4eb8044-d23e-41e0-9ebb-f7f2ab2a2954
Local pid:
pubs:331934
Deposit date:
2014-02-09

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