β,γ-不饱和酰胺与异铂衍生的 β,γ-不饱和 α-酮酯之间的不对称乙烯基迈克尔/六迈克尔串联反应

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI:10.1021/acs.joc.4c02066

Shan-Shan Xu, Zi-Yu Li, Meng-Yu Liu, Feng Sha, Xin-Yan Wu

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引用次数: 0

摘要

我们开发了一种有机催化的不对称乙烯基迈克尔/氧杂迈克尔串联反应，该反应介于β,γ-不饱和吡唑酰胺和异汀衍生的β,γ-不饱和酮酯之间，具有极佳的区域、非对映和对映选择性。该方法为构建含有三个连续手性中心的对映体纯的 3,4′-吡喃基螺吲哚衍生物提供了有效途径。此外，还研究了手性产物的转化，包括吡唑基团的去除和还原。

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Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters

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Asymmetric Vinylogous Michael/Oxa-Michael Tandem Reaction between β,γ-Unsaturated Amides and Isatin-Derived β,γ-Unsaturated α-Ketoesters

An organocatalytic asymmetric vinylogous Michael/oxa-Michael tandem reaction between β,γ-unsaturated pyrazoleamides and isatin-derived β,γ-unsaturated ketoesters has been developed with excellent regio-, diastereo-, and enantioselectivities. The methodology provides an effective approach to construct enantiomerically pure 3,4′-pyranyl spirooxindole derivatives containing three contiguous chiral centers. Moreover, the transformations of the chiral products, including the removal and reduction of the pyrazole group, have been investigated.

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来源期刊

The 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： The 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.