Asymmetric Assembly of Aromatic Rings To Produce Tetra-ortho-Substituted Axially Chiral Biaryl Phosphorus Compounds

Densely substituted title compounds can be obtained efficiently through an enantioselective [2+2+2] cycloaddition catalyzed by a cationic RhI/H8‐binap complex (see scheme). This method is highly practical in view of the ready access to substrates, mild reaction conditions, operational simplicity, an...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-01, Vol.46 (21), p.3951-3954
Main Authors: Nishida, Goushi, Noguchi, Keiichi, Hirano, Masao, Tanaka, Ken
Format: Article
Language:English
Subjects:
alkynes
biaryls
Catalysis
Crystallography, X-Ray
cycloaddition
Models, Molecular
Molecular Structure
Organometallic Compounds - chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
phosphorus
rhodium
Rhodium - chemistry
Stereoisomerism
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Summary:Densely substituted title compounds can be obtained efficiently through an enantioselective [2+2+2] cycloaddition catalyzed by a cationic RhI/H8‐binap complex (see scheme). This method is highly practical in view of the ready access to substrates, mild reaction conditions, operational simplicity, and high catalytic activity. cod=1,5‐cyclooctadiene; H8‐binap=2,2′‐bis(diphenylphosphanyl)‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐binaphthyl; Ts=p‐toluenesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200700064