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 palladium complex catalyzes two transformations in one pot: formation of
allylsilane from allyl trifluoroacetate using hexamethyldisilane and subsequent
imine allylation. A three-component reaction was developed where preformed
imines were replaced with aldehydes and anisidine. Under these reaction
conditions various aldehydes react smoothly to afford homoallylic amines.
R. E. Grote, E. R. Jarvo, Org. Lett., 2009,
11, 485-488.
An enantioselective synthesis of homoallylamides through reactions of stable and
easily accessible (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or
alkenyl-substituted N-phosphinoylimines is promoted by 1-5 mol % of
readily accessible NHC-Cu complexes, derived from C1-symmetric
imidazolinium salts. Allyl additions deliver the desired products in very good
yield and enantiomeric ratio.
E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 2011,
133, 3332-3335.
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.
