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Highly Diastereoselective C(sp 3 )C(sp) Cross‐Coupling Reactions between 1,3‐ and 1,4‐Substituted Cyclohexylzinc Reagents and Bromoalkynes through Remote Stereocontrol
Author(s) -
Thaler Tobias,
Guo LiNa,
Mayer Peter,
Knochel Paul
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.201006879
Subject(s) - diastereomer , stereoselectivity , reagent , chemistry , ligand (biochemistry) , combinatorial chemistry , derivative (finance) , coupling reaction , palladium , dopant , stereochemistry , catalysis , organic chemistry , doping , materials science , biochemistry , receptor , optoelectronics , financial economics , economics
Under the influence : The use of the readily available and inexpensive orthophenantroline derivative neocuproine as a ligand in the generally applicable and highly stereoselective palladium‐catalyzed title reaction results in diastereomeric ratios of up to 98:2. The method can be used for the synthesis of building blocks which may be relevant for the synthesis of liquid crystalline mesogens and their chiral dopants (see scheme, dba= trans , trans ‐dibenzylideneacetone).