氮杂烯烃与3-乙烯基吲哚的催化不对称形式[3+2]环加成反应：2,3-二氢吡咯的合成
Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.
作者信息
Mei Guang-Jian, Zheng Wenrui, Gonçalves Théo P, Tang Xiwen, Huang Kuo-Wei, Lu Yixin
机构信息
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
KAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia.
出版信息
iScience. 2020 Feb 21;23(2):100873. doi: 10.1016/j.isci.2020.100873. Epub 2020 Jan 31.
Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
手性磷酸催化的偶氮烯烃与3-乙烯基吲哚的高对映选择性形式[3 + 2]环加成反应已经建立。在温和条件下，预期的环加成反应顺利进行，以高产率和优异的对映选择性，并且以非对映体特异性方式得到了多种2,3-二氢吡咯。与先前文献报道中的常见4原子合成子不同，偶氮烯烃作为3原子合成子。此外，初步理论计算支持了观察到的选择性。本文所揭示的偶氮烯烃的独特化学性质将在更广泛的背景下推动含氮环结构基序的不对称合成。
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