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Enantioselective Dearomative Difunctionalization of Indoles by Palladium‐Catalyzed Heck/Sonogashira Sequence
Author(s) -
Liu RenRong,
Wang YongGang,
Li YingLong,
Huang BingBing,
Liang RenXiao,
Jia YiXia
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703833
Subject(s) - sonogashira coupling , enantioselective synthesis , stereocenter , phosphoramidite , palladium , chemistry , combinatorial chemistry , sequence (biology) , ligand (biochemistry) , catalysis , organic chemistry , receptor , dna , biochemistry , oligonucleotide
Palladium‐catalyzed enantioselective dearomative arylalkynylation of N‐substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL‐based phosphoramidite as the chiral ligand. A wide range of 2,3‐disubstituted indolines, bearing vicinal quaternary and tertiary stereocenters, were efficiently constructed in one step with excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (>20:1).