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Enantioselective Synthesis of Tetrahydropyrano[3,4‐ b ]indoles: Palladium(II)‐Catalyzed Aminopalladation/1,4‐Addition Sequence
Author(s) -
Chen Junjie,
Han Xiuling,
Lu Xiyan
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.201708900
Subject(s) - palladium , enantioselective synthesis , catalysis , intramolecular force , chemistry , yield (engineering) , sequence (biology) , aniline , combinatorial chemistry , stereochemistry , transition metal , medicinal chemistry , organic chemistry , materials science , biochemistry , metallurgy
A novel palladium(II)‐catalyzed cyclization of aniline‐tethered alkynyl cyclohexadienones is reported. This reaction offers an atom‐economical and redox‐neutral access to various cyclohexenone‐fused tetrahydropyrano[3,4‐ b ]indoles with high yield and excellent enantioselectivity. Remarkably, this work represents the first example on a transition‐metal‐catalyzed asymmetric intramolecular aminopalladation/1,4 addition sequence.