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Palladium‐Catalyzed Asymmetric Synthesis of Silicon‐Stereogenic 5,10‐Dihydrophenazasilines via Enantioselective 1,5‐Palladium Migration
Author(s) -
Sato Yosuke,
Takagi Chihiro,
Shintani Ryo,
Nozaki Kyoko
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.201705500
Subject(s) - palladium , stereocenter , enantioselective synthesis , catalysis , trimethylsilyl , ligand (biochemistry) , silicon , chemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry
A palladium‐catalyzed asymmetric synthesis of silicon‐stereogenic 5,10‐dihydrophenazasilines was developed that proceeds via an unprecedented enantioselective 1,5‐palladium migration. High enantioselectivity was achieved by employing 4,4′‐bis(trimethylsilyl) ( R )‐Binap as the chiral ligand, and a series of mechanistic investigations were carried out to probe the catalytic cycle of this process.