Highly Enantioselective γ-Amination by N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Oxidized Enals and Azodicarboxylates
Highly Enantioselective γ-Amination by N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Oxidized Enals and Azodicarboxylates
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DOI：
10.1002/anie.201305571
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发表时间：
2013-09-27
影响因子：
16.6
通讯作者：
Ye, Song
中科院分区：
文献类型：
--
作者：
Chen, Xiang-Yu;Xia, Fei;Ye, Song
在过去的十年中，N-杂环卡宾（NHC）催化已被广泛开发用于各种化学转化。[1, 2] 2004年，Bode等人。和格洛里斯等人。独立报道了通过 a3-d3 umpolung 方法通过 b-加成实现的开创性 NHC 催化的烯醇环化反应 [3+ 2]。 [3]此后，一系列NHC催化的烯醛的[3+n]成环反应被实现，用于合成一系列杂环和碳环化合物。[4, 5]还建立了NHC催化的烯醛加成的[2+4]成环反应。[6]2012年，Chi等人。报道了一种开创性的氧化 NHC 催化的烯醛与三氟甲基酮通过 g 加成的环化（方案 1 a）。 [7] 2011 年，我们报道了 NHC 催化的 a, b-不饱和酰氯与活化酮的 [4+ 2] 成环反应（Scheme1b）。 [8]我们设想将 NHC 添加到具有 Ag 离去基团的烯醛上可能会生成二烯醇盐中间体，这将
N-heterocyclic carbene (NHC) catalysis has been developed extensively for various chemical transformations over the past decade.[1, 2] In 2004, Bode et al. and Glorius et al. independently reported the pioneering NHC-catalyzed [3+ 2] annulation reaction of enals by b-addition through an a3-d3 umpolung approach.[3] Since then, a series of NHC-catalyzed [3+ n] annulation of enals has been realized for the synthesis of a range of hetero-and carbocyclic compounds.[4, 5] The NHC-catalyzed [2+ 4] annulation of enals by a addition was also established.[6]In 2012, Chi et al. reported a pioneering oxidative NHC-catalyzed [4+ 2] annulation of enals with trifluoromethyl ketones by g addition (Scheme 1 a).[7] In 2011, we reported an NHC-catalyzed [4+ 2] annulation of a, b-unsaturated acyl chlorides with activated ketones (Scheme1b).[8] We envisioned that the addition of an NHC to enals having ag leaving group may generate a dienolate intermediate, which would