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通过钯和布朗斯台德碱接力催化,由靛红的 Morita-Baylis-Hillman 碳酸酯和 -羟基烯酮构建二氢苯并呋喃骨架。

Construction of Hydrodibenzo[,]furan Frameworks from Morita-Baylis-Hillman Carbonates of Isatins and -Hydroxy Enones via Palladium and Brønsted Base Relay Catalysis.

机构信息

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.

出版信息

Org Lett. 2022 Jan 14;24(1):100-104. doi: 10.1021/acs.orglett.1c03689. Epub 2021 Dec 10.

DOI:10.1021/acs.orglett.1c03689
PMID:34889095
Abstract

A cascade assembly between isatin-derived Morita-Baylis-Hillman carbonates and -hydroxybenzylideneacetones has been developed under the relay catalysis of Pd(PPh) and DBU, affording a spectrum of 1,2,3,4-tetrahydrodibenzo[,]furan architectures incorporating a spirooxindole motif in moderate to good yields with excellent diastereoselectivity. The fused indole analogues were similarly furnished by employing the benzylideneacetones having an -TsNH group.

摘要

在 Pd(PPh) 和 DBU 的接力催化下,发展了一种色胺衍生的 Morita-Baylis-Hillman 碳酸酯和 -羟基苯亚甲基乙酮之间的级联组装反应,以中等至良好的收率和优异的非对映选择性,提供了一系列包含螺氧吲哚骨架的 1,2,3,4-四氢二苯并[,]呋喃结构。通过使用具有-TsNH 基团的苯亚甲基乙酮,同样可以得到稠合的吲哚类似物。

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