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Enantioselective Base‐Free Electrophilic Amination of Benzofuran‐2( 3H )‐ones: Catalysis by Binol‐Derived P ‐Spiro Quaternary Phosphonium Salts
Author(s) -
Zhu ChuanLe,
Zhang FaGuang,
Meng Wei,
Nie Jing,
Cahard Dominique,
Ma JunAn
Publication year - 2011
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.201100283
Subject(s) - enantioselective synthesis , phosphonium , amination , chemistry , electrophilic amination , benzofuran , catalysis , reactivity (psychology) , substrate (aquarium) , kinetic resolution , electrophile , combinatorial chemistry , organic chemistry , medicine , oceanography , alternative medicine , pathology , geology
A spiro ing reactivity : A series of novel binol‐derived P ‐spiro quaternary phosphonium salts were designed, prepared, and used for the first highly enantioselective amination of benzofuranones (see scheme; binol=1,1′‐2‐binaphthol, Bn=benzyl). An unprecedented mechanism involving the π–π interactions between the substrate and the catalyst was proposed as the primary binding mode on the basis of molecular modelling and DFT calculations.