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- Title
Amine Catalyzed Remote [4+2]‐annulation Of Indole Tethered Enal And Oxindole Olefin To Access Optically Pure Hydrocarbazole Spirooxindole Scaffolds.
- Authors
Prasad, Madavi S.; Ramesh, M.; Kumar Jha, Aman; Bharani, Sankar; Saha, Souvik; Bedanta, Thoudam; Chandrasekhar, Ponnada; Sarasija, M.
- Abstract
This research showcases a methodology for crafting highly intricate hydrocarbazole spirooxindole frameworks endowed with three consecutive stereocenters. Achieved through a trienamine‐catalyzed remote [4+2]‐annulation reaction, the method's significance is underscored by synthesizing an extensive array of library molecules (up to 27 examples). These compounds mimic natural products, exhibit good yields (up to 85 %), exceptional diastereo‐, enantiomeric ratios (up to 17 : 1 dr, 99.9 : 0.1 er). The practicality of our strategy is further exemplified by successfully synthesizing a hexahydroepoxyethanocarbazole spirooxindole scaffold via a sequential [4+2]‐annulation/‐reduction/epoxidation‐cyclization reaction, achieving a 75 % overall yield, maintaining an excellent stereoselectivity (99.5 : 0.5 er).
- Subjects
ALKENES; INDOLE; AMINES; NATURAL products; ENAMINES; STEREOSELECTIVE reactions
- Publication
Asian Journal of Organic Chemistry, 2024, Vol 13, Issue 6, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202400061