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Helicenes with Embedded Phosphole Units in Enantioselective Gold Catalysis
Author(s) -
Yavari Keihann,
Aillard Paul,
Zhang Yang,
Nuter Frédérick,
Retailleau Pascal,
Voituriez Arnaud,
Marinetti Angela
Publication year - 2014
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.201308377
Subject(s) - phosphole , enantioselective synthesis , catalysis , chemistry , enantiomer , combinatorial chemistry , transition metal , stereochemistry , nanotechnology , organic chemistry , materials science
This paper discloses the first uses of phosphahelicenes as chiral ligands in transition‐metal catalysis. Unlike all known helical phosphines used so far in catalysis, the phosphorus function of phosphahelicenes is embedded in the helical structure itself. This crucial structural feature originates unprecedented catalytic behaviors and efficiency. An appropriate design and fine tuning allowed both high catalytic activity and good enantiomeric excesses to be attained in the gold promoted cycloisomerizations of N‐tethered 1,6‐enynes and dien‐ynes.