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

…, AM Fletcher, L Lv, PM Roberts, JE Thomson

Index: Davies, Stephen G.; Fletcher, Ai M.; Lv, Linlu; Roberts, Paul M.; Thomson, James E. Tetrahedron Letters, 2012 , vol. 53, # 24 p. 3052 - 3055

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Citation Number: 26

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 ...