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炔烃取代的MBH碳酸酯的有机催化烯丙基烷基化反应:合成含季碳的1,4-烯炔

Organocatalytic allylic alkylation of alkyne-substituted MBH carbonates: access to quaternary carbon-containing 1,4-enynes.

作者信息

Li Yu, Wang Mei, Ma Rongrong, Niu Rui, Wang Haodong, Zhang Yantu, Lin Jun-Bing

机构信息

Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, China.

出版信息

Org Biomol Chem. 2023 Oct 25;21(41):8263-8266. doi: 10.1039/d3ob01317k.

Abstract

A DABCO-catalyzed allylic alkylation of tertiary propargylic alcohol-derived MBH carbonates with nitromethane was developed. A series of substituted 1,4-enynes with an all-carbon quaternary stereocenter were efficiently obtained in moderate to high yields. The synthetic utility of the product was demonstrated by facile synthesis of 1,4-enyne-embedded 2-pyrrolidinones.

摘要

开发了一种由DABCO催化的叔炔丙醇衍生的MBH碳酸酯与硝基甲烷的烯丙基烷基化反应。一系列带有全碳季碳立体中心的取代1,4-烯炔以中等到高的产率被高效合成。通过简便合成嵌入1,4-烯炔的2-吡咯烷酮证明了该产物的合成实用性。

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