Organocatalytic asymmetric reduction of N-unsubstituted β-enamino ester with HSiCl3

[Display omitted] The asymmetric reduction of N-unsubstituted β-enamino esters is the key step for catalytic asymmetric construction of sitagliptin, a prevalent drug for the treatment of type 2 diabetes. However, it is still lack of environment friendly, low-cost, nontoxic, and highly selective cata...

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Bibliographic Details
Published in:Tetrahedron letters 2023-06, Vol.122, p.154492, Article 154492
Main Authors: Liang, Yushi, Liang, Yumeng, Chen, Jingwen, Liu, Mingjie, Zhao, Zhenghua, Bao, Zongbi, Yang, Qiwei, Ren, Qilong, Zhang, Zhiguo
Format: Article
Language:English
Subjects:
Asymmetric reduction reaction
Lewis bases
N-unsubstituted β-enamino ester
Sitagliptin
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Summary:[Display omitted] The asymmetric reduction of N-unsubstituted β-enamino esters is the key step for catalytic asymmetric construction of sitagliptin, a prevalent drug for the treatment of type 2 diabetes. However, it is still lack of environment friendly, low-cost, nontoxic, and highly selective catalysts. Herein, we report a series of new silyl ether substituted l-pipecolinic formamides organocatalysts for the asymmetric reduction of N-unsubstituted β-enamino esters with trichlorosilane as the reducing agent. The steric hindrance of silyl ether substitutes can remarkably influence the catalytic performance. The optimized triphenylsilyl substituted catalyst 2k can efficiently catalyze the reduction reaction, affording enantioenriched β-amino ester with excellent yield (95 %) and high ee (82 %).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154492