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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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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:
400529
Keywords:
Pubs id:
pubs:400529
UUID:
uuid:72c9f46e-bb4b-4e9f-b1db-87304f3fae23
Local pid:
pubs:400529
Deposit date:
2013-11-16

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