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.
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 boronatesis
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 BF3ˇOEt2,
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.
