Divergent Asymmetric Synthesis of Chiral Spiroheterocycles through Pd-Catalyzed Enantio- and Diastereoselective [3 + 2] Spiroannulation

Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang Gi Lee

Research output: Contribution to journalArticlepeer-review

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Abstract

The palladium-catalyzed divergent asymmetric synthesis of chiral spiro-furanindoline derivatives is described. The zwitterionic alkoxy π-allyl Pd(II) intermediate, generated catalytically from vinyl ethylene carbonate (VEC), could undergo ligand-controlled enantio- and diastereoselective dipolar [3 + 2] spiroannulation with indole-based azadienes to afford the optically active spiro-furanindolines embedding an all-carbon quaternary stereocenter in high yields (up to 99%) with good to excellent stereoselectivities (up to 99% ee and up to >94:6 dr).

Original languageEnglish
Pages (from-to)9189-9193
Number of pages5
JournalOrganic Letters
Volume24
Issue number50
DOIs
StatePublished - 23 Dec 2022

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