Practical, Asymmetric Route to Sitagliptin and Derivatives: Development and Origin of Diastereoselectivity | Zendy

Osvaldo Gutiérrez | Zendy; Dattatray S. Metil | Zendy; Namrata Dwivedi | Zendy; Nagaraju Gudimalla | Zendy; E. R. R. Chandrashekar | Zendy; Vilas H. Dahanukar | Zendy; Apurba Bhattacharya | Zendy; Rakeshwar Bandichhor | Zendy; Marisa C. Kozlowski | Zendy

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Practical, Asymmetric Route to Sitagliptin and Derivatives: Development and Origin of Diastereoselectivity

Author(s) -

Osvaldo Gutiérrez,

Dattatray S. Metil,

Namrata Dwivedi,

Nagaraju Gudimalla,

E. R. R. Chandrashekar,

Vilas H. Dahanukar,

Apurba Bhattacharya,

Rakeshwar Bandichhor,

Marisa C. Kozlowski

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b00520

Subject(s) - chemistry , sitagliptin , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , diabetes mellitus , endocrinology , type 2 diabetes , medicine

The development of a practical and scalable process for the asymmetric synthesis of sitagliptin is reported. Density functional theory calculations reveal that two noncovalent interactions are responsible for the high diastereoselection. The first is an intramolecular hydrogen bond between the enamide NH and the boryl mesylate S═O, consistent with MsOH being crucial for high selectivity. The second is a novel C-H···F interaction between the aryl C5-fluoride and the methyl of the mesylate ligand.

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