Highly Diastereoselective C(sp 3 )C(sp) Cross‐Coupling Reactions between 1,3‐ and 1,4‐Substituted Cyclohexylzinc Reagents and Bromoalkynes through Remote Stereocontrol | Zendy

Thaler Tobias | Zendy; Guo LiNa | Zendy; Mayer Peter | Zendy; Knochel Paul | Zendy

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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).

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