Novel Axially Chiral Phosphine Ligand with a Fluoro Alcohol Moiety for Rh-Catalyzed Asymmetric Arylation of Aromatic Aldehydes

2010 ◽  
Vol 12 (11) ◽  
pp. 2520-2523 ◽  
Author(s):  
Satoshi Morikawa ◽  
Kyosuke Michigami ◽  
Hideki Amii
Keyword(s):  
Aromatic Aldehydes ◽  
Phosphine Ligand ◽  
Axially Chiral ◽  
Alcohol Moiety

An axially chiral phosphine ligand based on restricted rotation in N -arylimides

2001 ◽  
Vol 42 (41) ◽  
pp. 7185-7187 ◽  
Author(s):  
Yizhao Chen ◽  
Mark D Smith ◽  
Ken D Shimizu
Keyword(s):  
Phosphine Ligand ◽  
Restricted Rotation ◽  
Axially Chiral

Atropo-enantioselective synthesis of an axially chiral C1-symmetric phosphine ligand and its application in the asymmetric hydrosilylation of styrenes

1999 ◽  
Vol 10 (15) ◽  
pp. 3025-3031 ◽  
Author(s):  
Gerhard Bringmann ◽  
Andreas Wuzik ◽  
Matthias Breuning ◽  
Petra Henschel ◽  
Karl Peters ◽  
...  
Keyword(s):  
Phosphine Ligand ◽  
Enantioselective Synthesis ◽  
Axially Chiral

ChemInform Abstract: Phosphine Ligand Triggered Oxidative Decarbonylative Homocoupling of Aromatic Aldehydes: Selectively Generation Biaryls and Diarylketones.

ChemInform ◽  
2011 ◽  
Vol 42 (24) ◽  
pp. no-no
Author(s):  
Luo Yang ◽  
Tieqiang Zeng ◽  
Qi Shuai ◽  
Xiangyu Guo ◽  
Chao-Jun Li
Keyword(s):  
Aromatic Aldehydes ◽  
Phosphine Ligand

Synthesis of axially chiral bipyridine N,N'-dioxides and enantioselective allylation of aldehydes

2010 ◽  
Vol 82 (9) ◽  
pp. 1813-1826 ◽  
Author(s):  
Martin Kotora
Keyword(s):  
Reaction Mechanism ◽  
Aromatic Aldehydes ◽  
Synthetic Method ◽  
Chirality Transfer ◽  
Lewis Bases ◽  
Synthetic Strategy ◽  
Axially Chiral

N-oxides possessing the pyridine framework are strong Lewis bases that can activate the C–Si bond of allylhalosilanes to such an extent that they catalyze reactions with aldehydes. N-oxides embedded in chiral scaffolds are usually capable of highly selective chirality transfer to the derived products. Our goal was to develop a general synthetic method allowing the preparation of structurally varied N,N'-dioxides suitable for enantioselective organocatalysis. The underlying synthetic strategy was based on [2 + 2 + 2]-cyclotrimerization of suitably substituted diynes with nitriles catalyzed by Co-complexes to generate the desired bipyridines, their further oxidation and resolution of which furnished the corresponding chiral N,N'-dioxides. The prepared compounds were used in catalytic allylation of aromatic aldehydes to homoallyl alcohols with high enantioselectivity (up to 96 % ee). Enantioselectivity, enantiodiscrimination, and the reaction mechanism are controlled by the choice of solvent.

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