Categories: C-C Bond Formation > Amines, Arenes >
Diarylmethylamines
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Recent Literature
A highly efficient three-component coupling reaction between thioformamides and
organolithium and Grignard reagents was developed. The generality of the process
has been demonstrated by using various combinations of reactants and reagents.
T. Murai, F. Asai, J. Am. Chem. Soc., 2007,
129, 780-781.
A new type of C2-symmetric chiral diene ligand was applied
successfully in the Rh-catalyzed asymmetric arylation of N-tosylarylimines
with arylboronic acids to give a broad range of highly enantiomerically enriched
diarylmethylamines as well as 3-aryl substituted phthalimidines.
Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc., 2007,
129, 5336-5337.
The use of a new C2-symmetric diene ligand (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene
(Ph-bod*) for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines
with arylboroxines allowed asymmetric synthesis of diarylmethylamines with
high enantioselectivity.
N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc.,
2004, 126, 13584-13585.
The asymmetric arylation of N-tosylarylimines with arylboronic acids
was realized by using rhodium/(S)-ShiP as catalyst in aqueous toluene
to give diarylmethylamines in good yields and enantioselectivities.
H.-F. Duan, Y.-X. Jia, L-X. Wang, Q.-L. Zhou, Org. Lett.,
2006,
8, 2567-2569.
The asymmetric synthesis of diarylmethyl amines was realized by
rhodium-catalyzed asymmetric addition of aryl titanium reagents to
N-alkylidene sulfonamides.
T. Hayashi, M. Kawai, N. Tokunaga, Angew. Chem., 2004, 116,
6251-6252.
A selective rhodium/phosphoramidite-catalyzed synthesis of diarylmethyl
amines gave high enantioselectivities and high yields. The small and cheap
N,N-dimethylsulfamoyl protecting group was easily removed by a
microwave-assisted transamination.
R. B. C. Jagt, P. Y. Toullec, D. Geerdink, J. G. de Vries, B. L. Feringa, A.
J. Minnaard, Angew. Chem. Int. Ed., 2006,
45, 2789-2791.
