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Palladium‐Catalyzed Enantioselective Reductive Heck Reactions: Convenient Access to 3,3‐Disubstituted 2,3‐Dihydrobenzofuran
Author(s) -
Zhang ZhanMing,
Xu Bing,
Qian Yanyan,
Wu Lizuo,
Wu Yuanqi,
Zhou Lujia,
Liu Yu,
Zhang Junliang
Publication year - 2018
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.201806372
Subject(s) - enantioselective synthesis , stereocenter , heck reaction , phosphine , palladium , chemistry , combinatorial chemistry , aryl , catalysis , intramolecular force , ligand (biochemistry) , organic chemistry , alkyl , receptor , biochemistry
The first example of highly enantioselective intramolecular hydroarylation of allyl aryl ethers was realized by palladium‐catalyzed reductive heck reactions utilizing a new chiral sulfinamide phosphine ligand (N‐Me‐ XuPhos ). N‐Me‐ XuPhos can be easily prepared on gram scale from readily available starting materials in a one‐pot synthesis approach. A series of optically active 2,3‐dihydrobenzofurans bearing a quaternary stereocenter were obtained in good yields and with excellent enantioselectivities. The practicality of this reaction was validated in the straightforward synthesis of CB2 receptor agonists. Moreover, deuterium was efficiently incorporated into the products.