Categories: C-C Bond Formation > Oxygen-containing molecules > Alcohols >
Synthesis of homopropargylic alcohols
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Recent Literature
A rapid and efficient procedure for the solvent-free synthesis of
homoallylic and homopropargyl alcohols has been achieved by zinc-mediated
Barbier-type reaction of carbonyl compounds at room temperature.
J.-X. Wang, X. Jia, T. Meng, L. Xin,
Synthesis, 2005, 2669-2672.
The commercially available resin Amberlyst A-31 promotes a regio- and
chemoselective propargylation of aldehydes using potassium
allenyltrifluoroborate. This simple method gives products in short reaction
times in high yields and purity at room temperature.
T. R. Couto, J. J. R. Freitas, J. C. R. Freitas, I. H. Cavelcanti, P. H. Menezes,
R. A. Oliveira, Synthesis, 2015, 47,
71-78.
A highly enantioselective chiral Brønsted acid catalyzed propargylation of
aldehydes with allenylboronate allows a practical conversion of a broad range of
substrate covering aryl, polyaryl, heteroaryl, α,β-unsaturated, and aliphatic
aldehydes.
L. R. Reddy, Org. Lett., 2012,
14, 1142-1145.
3,3′-Br2-BINOL catalyze the enantioselective asymmetric
propargylation of ketones using allenyldioxoborolane as nucleophile, in the
absence of solvent, and under microwave irradiation to afford
homopropargylic alcohols in good yields and high enantiomeric ratios.
Diastereoselective propargylations using chiral racemic allenylboronates result
in good diastereoselectivities.
D. S. Barnett, S. E. Schaus, Org. Lett., 2011,
13, 4020-4023.
A propargylation of aldehydes and ketones with allenyl and propargyl boronates is
mediated by a catalytic amount of zinc. The propargylation with crystalline and
air-stable propargyl diethanolamine boronates was also achieved. A catalytic
cycle is proposed, and preliminary mechanistic studies are discussed.
D. R. Fandrick, K. R. Fandrick, J. T. Reeves, Z. Tan, C. S. Johnson, H. Lee, J.
J. Song, N. K. Yee, C. H. Senanayake, Org. Lett., 2010,
12, 88-91.
Trapping of β,γ-alkynyl aldehydes, generated in situ by treatment of
alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF3·OEt2,
by a variety of allyl nucleophiles affords homopropargylic homoallylic alcohols
in good yield and selectivity. Subsequent enyne metathesis gives functionalized
vinylcyclopentenols.
L. Wang, M. L. Maddess, M. Lautens, J. Org. Chem., 2007,
72, 1822-1825.
A readily available cyclopentadienyliron(II) dicarbonyl complex enables the
functionalization of propargylic and allylic C-H bonds via deprotonative
activation. Reactions of unsaturated building blocks with aryl aldehydes and
other carbonyl electrophiles provide a range of unsaturated alcohols under
operationally simple and functional group tolerant reaction conditions.
Y. Wang, J. Zhu, A. C. Durham, H. Lindberg, Y.-M. Wang, J. Am. Chem. Soc.,
2019, 141, 19594-19599.
A copper(I)-catalyzed asymmetric borylative propargylation of simple ketones
offers broad substrate scope, good tolerance of functional groups, high
diastereo- and enantioselectivities, and reaction robustness. The borylative
product can also serve as a cross-coupling partner in Pd-catalyzed
Suzuki-Miyaura reactions.
X.-C. Gan, L. Yin, Org. Lett., 2019, 21,
931-936.