Categories: C-C Bond Formation > Nitrogen-containing molecules > Synthesis of amines >
Homoallylamines
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Recent Literature

A general and mild CuCl-TBAT-catalyzed allylation of aldehydes, ketones, and
imines was developed using allyltrimethoxysilane as the allylating reagent.
Mechanism studies indicated that the copper alkoxide,
allylfluorodimethoxysilane, and allyltrimethoxysilane are essential to
promote the reaction efficiently.
S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc.,
2002,
124, 6536-6537.

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.

Homoallylic α-amino esters and amines were prepared via a Pd(II)-catalyzed
coupling of 1,2-nonadiene and boronic acids with ethyl iminoacetate or aliphatic,
aromatic, and heteroaromatic imines.
C. D. Hopkins, H. C. Malinakova, Org. Lett., 2006,
8, 5971-5974.

An asymmetric vinylogous Mannich reaction of α,α-dicyanoolefins and
N-Boc
aldimines is promoted by a simple chiral bifunctional thiourea-tertiary amine
organocatalyst. The reaction was highly efficient, regio-, and stereoselective
at room temperature for a broad range of substrates.
T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc., 2007,
129, 1878-1879.


