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Molecules 2018, 23(6), 1440;

Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate

College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, China
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Author to whom correspondence should be addressed.
Received: 3 June 2018 / Revised: 12 June 2018 / Accepted: 12 June 2018 / Published: 13 June 2018
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Optically pure sitagliptin phosphate monohydrate is efficiently and practically synthesized through a chiral hemiacetal as the key intermediate in 54% overall yield starting from (E)-4-(2,4,5-trifluorophenyl)but-2-enal and N-boc-protected hydroxylamine. The chiral hemiacetal fragment is constructed by a tandem aza-Michael/hemiacetal reaction catalyzed by an organocatalyst and the influence of acidity of Brønsted acid on tandem aza-Michael/hemiacetal reaction is researched in detail. View Full-Text
Keywords: sitagliptin phosphate monohydrate; aza-Michael/hemiacetal reaction; asymmetric synthesis sitagliptin phosphate monohydrate; aza-Michael/hemiacetal reaction; asymmetric synthesis

Scheme 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Gao, H.; Yu, J.; Ge, C.; Jiang, Q. Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate. Molecules 2018, 23, 1440.

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