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

Autor:	Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang-gi Lee
Rok vydání:	2022
Předmět:	Organic Chemistry Physical and Theoretical Chemistry Biochemistry
Zdroj:	Organic Letters. 24:9189-9193
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.2c03643
Popis:	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 to94:6 dr).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7a463f4c6fc3f10ff1d496963516f98f https://doi.org/10.1021/acs.orglett.2c03643 Zobrazit plný text záznamu