Enantioselective synthesis of chiral 4H-pyran derivatives through [3+3] tandem reaction over a squaramide catalyst

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI:10.1016/j.tetasy.2017.10.011

Zhonghe Wang, Yali Zhu, Jing Zhang, Jiawei Li, Min Wu, Xilong Yan, Yang Li, Ligong Chen

引用次数: 4

Abstract

An efficient [3+3] tandem reaction between 1-phenyl-3-methyl-5-pyrazolones and 2-(1-alkynyl)-2-alken-1-ones over a tertiary amine–squaramide catalyst is described. The pyran fused pyrazolone derivatives were successfully obtained in 53–88% yields and with 62–84% ee by this synthetic methodology. This methodology involves easily accessible starting material, mild condition, satisfied yields and ee values. Additionally, when enynes were used as the substrates for the [3+3] cascade reaction, isomerized target products could be obtained directly.

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方酰胺催化[3+3]串联反应手性4h -吡喃衍生物的对映选择性合成

报道了在叔胺-方酰胺催化剂上，1-苯基-3-甲基-5-吡唑啉酮和2-(1-炔基)-2-烯-1-酮之间的高效[3+3]串联反应。通过该合成方法，成功地获得了吡喃融合吡唑酮衍生物，产率为53 ~ 88%，ee为62 ~ 84%。该方法包括易于获取的起始材料、温和的条件、满意的产率和ee值。此外，当烯类作为底物进行[3+3]级联反应时，可以直接得到异构化的目标产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.