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Designed Ligands as Probes for the Catalytic Binding Mode in Mo‐Catalyzed Asymmetric Allylic Alkylation
Author(s) -
Trost Barry M.,
Dogra Kalindi,
Hachiya Iwao,
Emura Takashi,
Hughes David L.,
Krska Shane,
Reamer Robert A.,
Palucki Michael,
Yasuda Nobuyoshi,
Reider Paul J.
Publication year - 2002
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 - 10.1002/1521-3773(20020603)41:11<1929::aid-anie1929>3.0.co;2-o
Subject(s) - tsuji–trost reaction , allylic rearrangement , molybdenum , catalysis , amide , ligand (biochemistry) , chemistry , alkylation , nitrogen atom , stereochemistry , combinatorial chemistry , group (periodic table) , medicinal chemistry , organic chemistry , receptor , biochemistry
Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1 . Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.