Categories: C-C Bond Formation > Alcohols, Alkynes >
Synthesis of propargyl alcohols
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Recent Literature
Asymmetric alkynylation of aldehydes using catalytic amounts of
In(III)/BINOL enables a broad range of substrate generality with high
enantioselectivity due to the "bifunctional character" of the catalyst
activating both substrates.
R. Takita, K. Yakura, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc.,
2005,
127, 13760-13761.
Enantioselective additions of terminal acetylenes to aldehydes mediated by Zn(OTf)2
and (+)-N-methyl
ephedrine can be conducted in reagent grade toluene containing up to 1000 ppm H2O.
Products are isolated in high yield and high enantioselectivities.
D. Boyall, D. Frantz, E. M. Carreira, Org. Lett.,
2002, 4, 2605-2606.
Schiff-base amino alcohols derived from L-phenylglycine are highly effective
ligands for the enantioselective addition of phenylacetylene to aromatic
ketones to give optically active tertiary propargylic alcohols.
C. Chen, L. Hong, Z.-Q. Xu, L. Liu, R. Wang, Org. Lett.,
2006,
8, 2277-2280.
Commercially available 2 M Me2Zn in toluene is able to promote
the addition of phenylacetylene to aldehydes and ketones. This reactivity is
determined by a new mechanism, which is discussed. Broad scope, high
tolerance to functional groups, and a simple procedure make this new method
highly interesting.
P. G. Cozzi, J. Rudolph, C. Bolm, P.-O. Norrby, C. Tomasini, J. Org.
Chem., 2005,
70, 5733-5736.
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.
Inexpensive BINOL in combination with Ti(OiPr)4 catalyzes
the reaction of alkynylzinc reagents with a broad range of aldehydes to
generate chiral propargyl alcohols with high enantioselectivity at room
temperature.
L. Liang, T. T.-L. Au-Yeung, A. S. C. Chan, Org. Lett., 2002,
4, 3799-3801.
A new method for the coupling of aldehydes or ketones with alkynyl
propiolates in the absence of a base was developed. The reagents involved in
this coupling reaction are easy to handle and tolerate various functional
groups.
S. P. Shani, K. Koide, Angew. Chem. Int. Ed., 2004, 43,
2525-2527.
