ChemInform Abstract: Efficient Construction of Chiral Spiro[benzo[g]chromene‐oxindole] Derivatives via Organocatalytic Asymmetric Cascade Cyclization.

Pan, Feng‐Feng; Wei, Yu; Qi, Zheng‐Hang; Qiao, Chunhua; Wang, Xing‐Wang

doi:10.1002/chin.201441104

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2023

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“…However, there are no reports on metal-catalyzed asymmetric cascade annulations of the indoline-2-thiones. Herein, we describe the application of Bronsted base and Lewis acid cooperative activation [ 44 , 45 , 46 , 47 ] to the synthesis of spiro[indoline-3,4′-thiopyrano[2,3- b ]indole] derivatives via the Friedel–Crafts alkylation/cyclization tandem reactions of indoline-2-thiones and isatylidene malononitriles [ 48 , 49 , 50 , 51 ] ( Scheme 1 b).…”

Section: Introductionmentioning

confidence: 99%

Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-b]indole] Derivatives

et al. 2023

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With a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral spiro[indoline-3,4′-thiopyrano[2,3-b]indole] derivatives in good yields with excellent levels of enantioselectivities (up to 88% yield and 99% ee).

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