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 highly efficient asymmetric arylation of N-nosylimines with arylboronic
acids catalyzed by a rhodium-diene complex enables the synthesis of a wide range
of enantiopure N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one
in high yields under very mild conditions.
L. Wang. Z.-Q. Wang, M.-H. Xu, G.-Q. Lin, Synthesis, 2010,
3263-3264.
Monosubstituted C1-symmetric dicyclopentadienes as a new class
of diene ligands enable a rhodium-catalyzed asymmetric arylation of N-tosylarylimines
in excellent yields with high enantioselectivities. The preparation of these
diene ligands relied on an efficient lipase-catalyzed resolution as the key step.
C. Shao, H.-J. Yu, N.-Y. Wu, C.-G. Feng, G.-Q. Lin, Org. Lett., 2010,
12, 3820-3823.
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.
