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Palladium(0)‐Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate
Author(s) -
Ding Lu,
Gao RunDuo,
You ShuLi
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900425
Subject(s) - stereocenter , chemoselectivity , propargyl , enantioselective synthesis , chemistry , nucleophile , catalysis , intermolecular force , combinatorial chemistry , palladium , indole test , cascade reaction , organic chemistry , molecule
An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all‐carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee ) and chemoselectivity ( 3 / 4 >19:1 in most cases).