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有机/银双催化(3 + 2)/Conia-Ene 型环化:茚并螺环戊烯并氧吲哚的不对称合成。

Organo/Silver Dual Catalytic (3 + 2)/Conia-Ene Type Cyclization: Asymmetric Synthesis of Indane-Fused Spirocyclopenteneoxindoles.

机构信息

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, PR China.

State Key Laboratory of Biotherapy and Department of Pharmacy, West China Hospital, Sichuan University, Chengdu 610041, PR China.

出版信息

Org Lett. 2022 Aug 26;24(33):6197-6201. doi: 10.1021/acs.orglett.2c02472. Epub 2022 Aug 17.

Abstract

Developing efficient strategies to synthesize spirocyclopenteneoxindoles is an attractive target due to their potential biological activity. This work described the thiourea/silver dual catalytic (3 + 2)/Conia-ene type reaction of 2-(2-oxoindolin-3-yl)malononitrile with -ethynyl substituted nitrostyrene. The reaction features mild conditions and good atom- and step-economy. Three new C-C bonds were formed within one synthetic step, providing the indane-fused spirocyclopenteneoxindoles in good yields, with excellent chemo-, regio-, and stereoselectivity.

摘要

由于螺环戊烯并吲哚类化合物具有潜在的生物活性,因此开发有效的方法来合成它们是一个很有吸引力的目标。本工作描述了硫脲/银双催化(3 + 2)/Conia-ene 型反应,该反应可用于 2-(2-氧代吲哚啉-3-基)丙二腈与 -乙炔基取代的硝代苯乙烯的反应。该反应条件温和,具有良好的原子经济性和步骤经济性。在一步合成中形成了三个新的 C-C 键,以良好的收率得到了茚并稠合的螺环戊烯并吲哚类化合物,具有优异的化学选择性、区域选择性和立体选择性。

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