Categories: C-N Bond Formation > Amines >
Synthesis of propargylic amines
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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.
N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew.
Chem., 2003, 115, 5941-5944.
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.
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.
C. Wei, C.-J. Li, J. Am. Chem. Soc., 2003,
125, 9584-9585.
A three-component coupling between an aldehyde, alkyne and amine 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.
A three-component coupling reaction of alkynylsilanes, aldehydes and amines
produces a variety of propargyl amine derivatives by a cooperative catalytic
system comprised of CuCl and Cu(OTf)2. This catalytic system was
successfully applied to the practical preparation of 1,6-diyne derivatives
via twice-performed, domino-type coupling reactions.
N. Sakai, N. Uchida, T. Konakahara, Synlett, 2008,
1515-1519.
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.
L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem.,
2006,
71, 1558-1562.
A general and efficient FeCl3-catalyzed substitution reaction of
propargylic alcohols with carbon- and heteroatom-centered nucleophiles such
as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides,
forms new C-C, C-O, C-S and C-N bonds.
Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006,
71, 8298-8301.
