β-酮酰基吡唑作为 2C 合成子在正羟基查耳酮不对称环化中的应用：反式-3,4-二氢香豆素的立体选择性构建

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-12-10 DOI:10.1021/acs.joc.4c0132710.1021/acs.joc.4c01327

Liying Cui*, Xiaofeng Yang, Changchun Yuan and Zhenghong Zhou*,

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Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins

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Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins

An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with o-hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (>19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.