Dethe Dattatraya H, Beeralingappa Nagabhushana C, Das Saikat, Nirpal Appasaheb K
Department of Chemistry, Indian Institute of Technology Kanpur Kanpur 208016 India
Chem Sci. 2021 Feb 2;12(12):4367-4372. doi: 10.1039/d0sc06845d.
Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed isomerization followed by C(allyl)-H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent regio- and diastereoselectivity ensure universality of the reaction. In addition, the unique power of this reaction was illustrated by performing the Diels-Alder reaction, and enantioselective synthesis of highly functionalized cyclohexenone and piperidine and finally synthetic utility was further demonstrated by the efficient synthesis of norpyrenophorin, an antifungal agent.
已开发出铑催化的烯丙基硅烷和烯丙基酯与活性烯烃的氧化偶联反应,该反应通过异构化然后进行C(烯丙基)-H活化,能够以优异的产率高效合成立体规整的1,3-二烯。温和的反应条件、较便宜的催化剂以及出色的区域和非对映选择性确保了该反应的通用性。此外,通过进行狄尔斯-阿尔德反应以及对高官能化环己烯酮和哌啶的对映选择性合成,展示了该反应的独特优势,最终通过高效合成抗真菌剂诺吡菌素进一步证明了其合成实用性。