Categories: C-C Bond Formation > Oxygen-containing molecules > Carboxylic Acids and Derivatives
Allylations
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Recent Literature
A Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reaction of
aryl ynol ethers and ynamides with allylic alcohols provides γ,δ-unsaturated
esters or amides, respectively. The [Au(IPr)NTf2] catalyst is most
effective for this reaction, and the reaction proceeds under mild conditions in
an atom-economical way.
S. Misawa, A. Miyairi, Y. Oonoshi, S. P. Nolan, Y. Sato, Synthesis, 2021, 53,
4644-4645.
Copper-catalyzed allylic alkylation of ketene silyl acetals proceeds with
excellent γ-E-selectivity. In reactions of enantioenriched secondary
allylic phosphates, an efficient α-to-γ chirality transfer with anti-selectivity
can be achieved. The reaction was readily scalable and highly reliable in terms
of product yield and stereoselectivities.
D. Li, H. Ohmiya, M. Sawamura, Synthesis, 2012, 44,
1304-1307.
Diallyl 2-alkyl-2-arylmalonates underwent palladium-catalyzed decarboxylative
allylation quickly under mild conditions. In contrast, no reaction took place
with diallyl 2,2-dialkylmalonates under the same conditions. Electron-donating
phosphine ligands were found to be vital for this reaction.
D. Imao, A. Itoi, A. Yamazaki, M. Shirakura, R. Ohtoshi, K. Ogata, Y. Ohmori, T.
Ohta, Y. Ito, J. Org. Chem., 2007,
72, 1534-1537.
Cooperative catalysis facilitates the direct asymmetric α-allylation of readily
available aryl acetic acid esters. Since enantioselection is determined by a
chiral nucleophile, this conceptual approach to cooperative catalysis
constitutes a potentially general solution to the direct catalytic asymmetric
α-functionalization of acyclic esters.
K. J. Schwarz, J. L. Amos, J. C. Klein, D. T. Do, T. N. Snaddon, J. Am. Chem. Soc., 2016,
138, 5214-5217.
A efficient copper-catalyzed cross-coupling of allyl phosphate with
2-fluoro-2-(trimethylsilyl)acetate provides a series of monofluoroalkylation
products in high yields.
Y. Liu, R. Chen, L. Lu, D. Yin, F. Yan, X.-X. Li, H. Xiao, S. Fun, S. Fun,
Y.-S. Feng, J. Org. Chem., 2023, 88,
7469-7476.
The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor
rhodium carbenoids and chiral allyl alcohols generates two vicinal stereogenic
centers in a convergent C-C bond forming process. Any of the four possible
stereoisomers can be selectively synthesized by appropriate combination of the
chiral catalyst Rh2(DOSP)4 and the chiral alcohol.
Z. Li, B. T. Parr, H. M. L. Davies, J. Am. Chem. Soc., 2012,
134, 10942-10946.
Chelated amino acid ester enolates are excellent nucleophiles for allylic
alkylations. With these enolates, even terminal π-allyl palladium complexes react
without significant isomerization.
K. Krämer, U. Kazmaier, J. Org. Chem., 2006,
71, 8950-8953.
Cocatalysis between a chiral Ir-(phosphoramidite,olefin) complex and La(OTf)3
enables enantioselective bond formation between sterically hindered racemic
tertiary α-allenyl alcohols and tetrasubstituted silyl ketene acetals to provide
β-allenyl ester products in good yield and with excellent enantioselectivity.
M. Isomura, D. A. Petrone, E. M. Carreira, J. Am. Chem. Soc.,
2021, 143, 3323-3329.
A gold-catalyzed reaction of sulfonium and selenium ylides with
aryldiazoacetates provides products of a [2,3]-sigmatropic rearrangement in high
yields. A reaction of aryl allyl anilines delivers exclusively C-H functionalized products.
F. He, S. Jana, R. M. Koenigs, J. Org. Chem., 2020, 85,
11882-11891.