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A combined experimental and computational study of NHC-catalyzed allylation of allenoate with MBH esters: new regiospecific and stereoselective access to 1,5-enyne
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2021-11-09 , DOI: 10.1039/d1qo01083b
Fang Sun 1 , Fangfang Lu 1 , Xue Song 1 , Wenchao Wu 1 , Kai Zhang 1 , Chenxia Yu 1 , Tuanjie Li 1 , Donghui Wei 2 , Changsheng Yao 1
Affiliation  

An NHC-catalyzed regiospecific allylation of α-substituted allenoates with MBH carbonates derived from aryl aldehyde furnished highly functionalized 1,5-enynes bearing a quaternary carbon successfully. Combining with DFT calculations, the reaction mechanism of this conversion was proposed. This method has the advantages of high regioselectivity, good yields and mild reaction conditions. This transformation not only provided a new access to 1,5-enyne, but also enriched the chemistry of allenoates and NHC catalysis.

中文翻译:

NHC 催化烯丙酸与 MBH 酯烯丙基化的实验和计算研究:新的区域特异性和立体选择性获得 1,5-烯炔

NHC 催化的α-取代的烯丙酸酯与衍生自芳醛的 MBH 碳酸酯的区域特异性烯丙基化成功地提供了带有季碳的高度官能化的 1,5-烯炔。结合DFT计算,提出了这种转化的反应机理。该方法具有区域选择性高、收率好、反应条件温和等优点。这种转变不仅提供了获得 1,5-烯炔的新途径,而且丰富了烯丙酸和 NHC 催化的化学性质。
更新日期:2021-12-01
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