Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles
Guang-Jian Mei,
Wenrui Zheng,
Théo P. Gonçalves,
Xiwen Tang,
Kuo-Wei Huang,
Yixin Lu
Affiliations
Guang-Jian Mei
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Wenrui Zheng
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Théo P. Gonçalves
KAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia
Xiwen Tang
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Kuo-Wei Huang
KAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia
Yixin Lu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore; Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, Fujian 359297, PR China; National University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Suzhou, 215123, China; Corresponding author
Summary: 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. : Organic Chemistry; Organic Synthesis; Physical Organic Chemistry Subject Areas: Organic Chemistry, Organic Synthesis, Physical Organic Chemistry
