Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles

• Published in: iScience Vol. 23; no. 2; p. 100873
• Main Authors: Mei, Guang-Jian, Zheng, Wenrui, Gonçalves, Théo P., Tang, Xiwen, Huang, Kuo-Wei, Lu, Yixin
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 21.02.2020; Elsevier
• Subjects: Organic Chemistry; Organic Synthesis; Physical Organic Chemistry; Physical Organic Chemistry; Organic Synthesis; Organic Chemistry
• ISSN: 2589-0042; 2589-0042
• DOI: 10.1016/j.isci.2020.100873

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. [Display omitted] •Chiral phosphoric acid catalyzed formal [3 + 2] cycloaddition reaction•2,3-Dihydropyrroles were enantioselectively synthesized•Azoalkenes served as 3-atom synthons Organic Chemistry; Organic Synthesis; Physical Organic Chemistry