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膦催化串联多米诺 1,6-加成/环化反应：构建具有炔基取代的全碳季碳中心的官能化色满和四氢喹啉。

Phosphine Sequentially Catalyzed Domino 1,6-Addition/Annulation: Access to Functionalized Chromans and Tetrahydroquinolines with an Ethynyl-Substituted All-Carbon Quaternary Center.

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , China.

Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 300071 , China.

出版信息

Org Lett. 2019 Feb 15;21(4):908-912. doi: 10.1021/acs.orglett.8b03819. Epub 2019 Jan 30.

DOI:10.1021/acs.orglett.8b03819
PMID:30698451
Abstract

A novel phosphine sequentially catalyzed domino 1, 6-addition/annulation process has been developed using p-quinone methides ( p-QMs) and α-substituted allenoates which generates a series of chroman and tetrahydroquinoline derivatives containing an ethynyl-substituted all-carbon quaternary center with up to 97% yield and 20:1 dr. value. In this reaction, allenoates act as C2 synthons.

摘要

一种新型膦催化的串联 1,6-加成/环化反应已被开发出来，用于 p-醌甲醚（p-QMs）和α-取代的丙二烯酸酯，生成一系列含有乙炔基取代的全碳季碳中心的色满和四氢喹啉衍生物，产率高达 97%，dr 值为 20:1。在这个反应中，丙二烯酸酯充当 C2 合成子。

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