Conjugated Nitrodienes. Synthesis and Reactivity

Abstract

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Cover Picture: Exploring the Potential Energy Surface of E2P4 Clusters (E=Group 13 Element): The Quest for Inverse Carbon‐Free Sandwiches (Chem. Eur. J. 16/2014)

“…Next, we focused on the synthesis of 2‐styryl‐substituted carbazole derivatives by using synthetically challenging polyconjugated nitro olefins as Michael acceptors 8. The results revealed that the reaction between indole derivatives 1a and 1b and α‐alkyl‐δ‐aryl‐substituted nitro‐dienes 2aq and 2br – 2bt took place exclusively at the β‐position of the nitro‐dienes under our typical reaction conditions.…”

Applications of Thermal Activation, Ball‐milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides

“…Further reaction of the adducts led to 1,5-diketones with three contiguous stereocenters after hydration/Michael cyclization sequences. [17] Therefore, the methods proposed herein are seen as a valuable alternative approach to these interesting adducts by combining stable, crystalline acceptors together with low catalyst loadings. [15] However, such Michael additions relied on iminium-ion catalysis and required as much as 15 mol% of intricate chiral bifunctional primary amine-thiourea catalysts.…”

“…[16a] This approach is further complicated by the limited stability of polyconjugated nitroalkenes. [17] Therefore, the methods proposed herein are seen as a valuable alternative approach to these interesting adducts by combining stable, crystalline acceptors together with low catalyst loadings.…”

“…However, such Michael additions relied on iminium‐ion catalysis and required as much as 15 mol% of intricate chiral bifunctional primary amine‐thiourea catalysts . This approach is further complicated by the limited stability of polyconjugated nitroalkenes …”

Recent Progress on Polyconjugated Nitrodienynes/Nitroenynes:Synthesis and Applications

“…而且, 由于其共轭体系的存在, 反应中存在 多个亲电反应位点, 从而引入了区域选择性竞争反应可 能, 如 1,4-加成反应、1,6-加成反应甚至 1,8-加成反应. 2013 年, Román 课题 组 [7] 对硝基二烯的合成与反应做 了详尽的综述. 基于作者前期的研究, 本文将对多共轭 硝基二烯炔/硝基烯炔的合成及其在有机合成中的应用 研究进行综述.…”