由于对映体纯化合物的高需求,烯烃不对称氢化的研究在药物分子合成和化学工业中都具有重要意义。所建立的方法通常需要几何纯烯烃。对映聚合反应提供了通过E/Z-烯烃混合物的氢化获得单一立体异构体的可能性;然而,碳-碳双键旁边的极性官能团通常是必要的。
该文中,研究人员报道了钴催化的易得的最小官能化E/Z-烯烃混合物的对映聚合氢化。该策略显示了良好的官能团耐受性,并提供了对映收敛转化的替代手段。初步的机理研究表明,钴催化异构化是实现会聚转化的关键。
附:英文原文
Title: Cobalt-Catalyzed Enantioconvergent Hydrogenation of Minimally Functionalized Isomeric Olefins
Author: Peng Lu, Hongliang Wang, Yihui Mao, Xin Hong, Zhan Lu
Issue&Volume: September 15, 2022
Abstract: Investigation on asymmetric hydrogenation of olefins is of great importance in both pharmaceutical molecule synthesis and chemical industry due to the high demand for enantiopure compounds. The established methods often require geometrically pure olefins. The enantioconvergent reaction provided the possibility to access a single stereoisomer via hydrogenation of E/Z-olefin mixtures; however, a polar functional group next to the carbon–carbon double bond was usually necessary. Here, we reported a cobalt-catalyzed enantioconvergent hydrogenation of readily available minimally functionalized E/Z-olefin mixtures. This strategy shows good functional group tolerance and provides an alternative means to enantioconvergent transformation. The preliminary mechanistic studies indicated that cobalt-catalyzed isomerization was the key to achieve the convergent transformation.
DOI: 10.1021/jacs.2c08525
Source: https://pubs.acs.org/doi/10.1021/jacs.2c08525
JACS:《美国化学会志》,创刊于1879年。隶属于美国化学会,最新IF:14.612
官方网址:https://pubs.acs.org/journal/jacsat
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