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Keywords = aza-Michael/hemiacetal reaction

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12 pages, 1216 KiB  
Article
Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate
by Haoling Gao, Jiangang Yu, Chengsheng Ge and Qun Jiang
Molecules 2018, 23(6), 1440; https://doi.org/10.3390/molecules23061440 - 13 Jun 2018
Cited by 14 | Viewed by 8115
Abstract
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 [...] Read more.
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. Full article
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