Categories: C-C Bond Formation > Amines, Alkynes >
Propargylamines and amides
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A copper(I) complex of i-Pr-pybox-diPh efficiently catalyzes the
enantioselective one-pot three-component synthesis of propargylamines from
aromatic aldehydes, anilines, and alkynes. A transition-state model has been
proposed.
A. Bisai, V. K. Singh, Org. Lett.,
2006,
8, 2405-2408.
A wide range of chiral propargylamines can be prepared in a one-pot
three-component reaction between an alkyne, an aldehyde and a secondary amine at
room temperature in the presence of CuBr and (R)-quinap in good yield and
good enantioselectivity. Remarkably, the copper-catalyzed reaction is highly diastereoselective if a
chiral amine or aldehyde is used.
N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem. Int. Ed.,
2003,
42, 5763-5766.
A highly efficient gold-catalyzed three-component-coupling of aldehydes,
alkynes, and amines in water was developed. Excellent yields of the
corresponding propargylamines were obtained in most cases for both aromatic
and aliphatic aldehydes and various amines.
V. K.-Y. Lo, Y. Liu, M.-K. Wong, C.-M. Che, Org. Lett.,
2006,
8, 1529-1532.
A novel InBr3-Et3N reagent system promotes the alkynylation of
not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but
also N,O- or N,S-acetals. The reaction of N-silyl-N,O-acetals
with
1-alkynes gives primary propargylic amines in
good yields.
N. Sakai, R. Kanada, M. Hirasawa, T. Konakahara, Tetrahedron, 2005,
61, 9298-9304.
N. Sakai, R. Kanada, M. Hirasawa, T. Konakahara, Tetrahedron, 2005,
61, 9298-9304.
A simple and effective copper-catalyzed oxidative cross-coupling of
dimethylanilines with alkynes in the presence of tert-BuOOH allows
the construction of propargylamines via a combination of sp3 C-H
bond and sp C-H bond activations followed by C-C bond formation.
Z. Li, C.-J. Li, J. Am. Chem. Soc.,
2004,
126, 11810-11811.
Highly enantioselective direct alkyne-imine additions catalyzed by Cu(I)OTf
and Evan's pybox ligands were developed in water and in toluene. The process
is simple and allows the synthesis of various propargylic amines in high ees
and good yields.
C. Wei, C.-J. Li, J. Am. Chem. Soc., 2002,
124, 5638-5639.
Propargylamines have been synthesized by a gold(III) salen complex-catalyzed
three-component coupling reaction of aldehydes, amines, and alkynes in water
in excellent yields at 40°C. With chiral prolinol derivatives as the amine
component, excellent diastereoselectivities have been attained.
V. K.-Y. Lo, Y. Liu, M.-K. Wong, C.-M. Che, Org. Lett.,
2006,
8, 1529-1532.
MgI2 as an additive enables a dramatic improvement in the [IrCl(COD)]2-catalyzed
addition reaction of silylacetylenes and imines. This general and convenient
reaction provides various amine products in excellent yields and can be
conducted in THF as well as in the absence of solvent.
C. Fischer, E. M. Carreira, Synthesis, 2004,
1497-1503.
A highly enantioselective, catalytic three-component coupling of aldehydes,
alkynes, and 4-piperidone hydrochloride hydrate affords the corresponding
tertiary propargylamines in useful yields. A selective cleavage of the
piperidone protecting group is possible using either ammonia/EtOH or a
polymer-supported scavenger amine.
P. Aschwanden, C. R. J. Stephenson, E. M. Carreira, Org. Lett.,
2006,
8, 2437-2440.
The three-component coupling of aldehyde, alkyne and amines is catalyzed
by silver iodide to generate propargylic amines in high yields in water
without cocatalyst or activator. This method is especially effective for
reactions involving aliphatic aldehydes.
C. Wei, Z. Li, C.-J. Li, Org. Lett., 2003,
5, 4473-4475.
Treatment of various aromatic and aliphatic aldimines with a mixture of a
terminal alkynes and dimethylzinc solution in toluene yields the
corresponding protected propargylic amines in moderate to excellent yields.
A three-component synthesis of propargylic amines with an aldehyde, ortho-methoxyaniline
and phenylacetylene through in situ formation of the corresponding imine in
the presence of dimethylzinc was developed.
L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem.,
2006,
71, 1558-1562.
L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem.,
2006,
71, 1558-1562.
A rapid copper-catalyzed three-component coupling of imines with alkynes
and acid chlorides to prepare propargylamides is described. The use of
chloroformates instead of acid chlorides allows the preparation of N-carbamate-protected
propargylamines.
D. A. Black, B. A. Arndtsen, Org. Lett., 2004,
6, 1107-1110.
A mild, copper(I)/Quinap-catalyzed addition of functionalized alkynes to
enamines in high yields and with up to 90% ee is reported. Some selective
transformations of the propargylamine products show the potential synthetic
utility of this method.
C. Koradin, K. Polborn, P. Knochel, Angew. Chem.,
2002, 114, 2651-2654.
