Asymmetric carbon-carbon coupling of phenols or anilines with aryllead triacetates.
The asymmetric coupling of various phenol or aniline derivatives with bulky aryllead triacetates was thoroughly investigated using optically active amines, including strychnine and brucine. We found that conformationally restricted tertiary amines, as well as lithium aryloxides and molecular sieves, are essential for accelerating the rate of phenol coupling. Consequently, the reaction can be carried out at a low temperature (-40 to -20 degrees C) and gives a high degree of diastereo- and enantioselectivity. In contrast to the effectiveness of lithiation in phenol coupling, magnesation of anilines was a critical technique for aniline coupling with aryllead triacetates. Using these coupling methods, a diverse set of di-, tri, and polyaryl compounds with axial chirality can be easily obtained, and these should be useful for the construction of a variety of aryl-aryl frameworks involved in metal ligands, natural products, and artificial helical polymers.
Kano
Taichi
T
Contribution from the Graduate School of Engineering, Nagoya University, SORST, Japan.
Ohyabu
Yuki
Y
Saito
Susumu
S
Yamamoto
Hisashi
H
D000588:Amines / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013331:Strychnine / Q000031:analogs & derivatives* / Q000737:chemistry
D000588:Amines; D000814:Aniline Compounds; D009942:Organometallic Compounds; D010636:Phenols; D011084:Polycyclic Aromatic Hydrocarbons; C083806:brucine; D013331:Strychnine; C008261:lead acetate