Chiral Spirocyclic Phosphoric Acid‐Catalyzed Synthesis of 4‐Alkyl‐3,4‐dihydropyrimidin‐2(1H)‐one Derivatives by Asymmetric Biginelli Reactions,Asian Journal of Organic Chemistry

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Chiral Spirocyclic Phosphoric Acid‐Catalyzed Synthesis of 4‐Alkyl‐3,4‐dihydropyrimidin‐2(1H)‐one Derivatives by Asymmetric Biginelli Reactions
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-02-20 , DOI: 10.1002/ajoc.201900718
Yongbiao Guo ₁ , Zhenhua Gao ₁ , Kang Wang ₁ , Junchen Li ₁ , Xiaojing Bi ₁ , Lei Guo ₁ , Haibo Liu ₁ , Enxue Shi ₁ , Junhua Xiao ₁

Affiliation

A chiral spirocyclic phosphoric acid‐catalyzed asymmetric Biginelli reaction based on aliphatic aldehydes has been realized for the synthesis of biologically important and synthetically useful 4‐alkyl‐3,4‐dihydropyrimidin‐2‐(1H)‐one (4‐alkyl−DHPM) skeletons in good yield and with high levels of enantioinduction. The utility of this transformation was further demonstrated by direct thionation and C−C/C−N bond construction to provide a series of 4‐alkyl−DHPMs derivatives without any loss of optical activity, providing streamlined access to the formal synthesis of Batzelladine A.

中文翻译：

手性螺环磷酸催化不对称Biginelli反应合成4-烷基-3,4-二氢嘧啶-2（1H）-one衍生物

已经实现了基于脂族醛的手性螺环磷酸催化的不对称Biginelli反应，用于合成生物学上重要且可合成的4-烷基-3,4-二氢嘧啶-2-（1H）-一（4-烷基-DHPM）骨架，产量高，对映体诱导水平高。通过直接硫磺化和C-C / C-N键结构进一步证明了这种转化的效用，从而提供了一系列4-烷基-DHPMs衍生物，而没有任何光学活性的损失，为简化的Batzelladine A的正式合成提供了途径。

更新日期：2020-04-21

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