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Enantioselective Difunctionalization of Alkenes by a Palladium‐Catalyzed Heck/Sonogashira Sequence
Author(s) -
Zhou Lujia,
Li Sanliang,
Xu Bing,
Ji Danting,
Wu Lizuo,
Liu Yu,
Zhang ZhanMing,
Zhang Junliang
Publication year - 2020
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.201913367
Subject(s) - stereocenter , sonogashira coupling , palladium , enantioselective synthesis , chemistry , combinatorial chemistry , intramolecular force , catalysis , propargyl , sequence (biology) , organic chemistry , biochemistry
Sonogashira‐type cross‐couplings are one of the most significant alkynylations in organic chemistry. One of the first palladium‐catalyzed intramolecular Heck/Sonogashira reactions of alkenes with terminal alkynes is now reported. With this method, a variety of uniquely substituted chiral benzene‐fused heterocycles bearing a propargyl‐substituted all‐carbon quaternary stereocenter were obtained in a straightforward, high‐yielding, and highly stereoselective manner under mild conditions. Salient features of this process include the use of readily available substrates, high selectivities, a broad substrate scope as well as versatile product functionalizations.