- A further step to sustainable palladium catalyzed oxidation: Allylic oxidation of alkenes in green solvents
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The palladium catalyzed oxidation of alkenes with molecular oxygen is a synthetically important reaction which employs palladium catalysts in solution; therefore, a solvent plays a critical role for the process. In this study, we have tested several green solvents as a reaction medium for the allylic oxidation of a series of alkenes. Dimethylcarbonate, methyl isobutyl ketone, and propylene carbonate, solvents with impressive sustainability ranks and very scarcely exploited in palladium catalyzed oxidations, were proved to be excellent alternatives for the solvents conventionally employed in these processes, such as acetic acid. Palladium acetate alone or in the combination with p-benzoquinone efficiently operates as the catalyst for the oxidation of alkenes by dioxygen under 5–10 atm. For most substrates, the systems in green solvents showed better selectivity for allylic oxidation products as compared to pure acetic acid; moreover, the reactions in propylene carbonate solutions occurred even faster than in acetic acid.
- dos Santos Costa, Maíra,de Camargo Faria, Amanda,Mota, Rayssa L.V.,Gusevskaya, Elena V.
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- Base-induced decarboxylation of polyunsaturated α-cyano acids derived from malonic acid: Synthesis of sesquiterpene nitriles and aldehydes with β-, φ-, and ψ-end groups
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Catalytic base-induced decarboxylation of polyunsaturated α-cyano-β-methyl acids derived from malonic acid led to the corresponding nitriles 3 (Schemes 2 and 3), 6 (Scheme 5), and 9 (Scheme 6). This decarboxylation occurred with previous deconjugation of
- Dufossé, Laurent,Cartier, Dominique,Valla, Benoist,Fouillaud, Mireille,Labia, Roger,Valla, Alain
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p. 259 - 265
(2013/03/28)
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- A new biomimetic-like aromatization of the cyclic end groups of terpenoids with stereospecific migration of one of the methyl groups: A convenient route to isorenieratene (φ,φ-carotene)
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The synthesis of isorenieratene, a natural carotenoid isolated from the marine sponge Reniera japonica and from some anoxygenic phototrophic bacteria or nonphotosynthetic actinomycetes, was performed from α-, β- and retro-ionones. In this series of cycloh
- Valla, Alain,Andriamialisoa, Zo,Valla, Benoist,Labia, Roger,Le Guillou, Regis,Dufosse, Laurent,Cartier, Dominique
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p. 711 - 715
(2007/10/03)
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- Selectivity in palladium catalyzed arylation: Synthetic application leading to aromatized ionone natural products
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The selectivity in aromatic substitution vs conjugate addition during palladium catalyzed reactions has been controlled simply by changing the base. These reaction conditions have been applied to the syntheses of aromatized β-ionone natural products 1 and its dihydroderivatives 7.
- Hagiwara, Hisahiro,Eda, Yasushi,Morohashi, Kimie,Suzuki, Toshio,Ando, Masayoshi,Ito, Nobuhiko
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p. 4055 - 4058
(2007/10/03)
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- A new synthesis of 4-(2,3,6-trimethylphenyl)butan-2-ol, a C13-norisoprenoid artifact from Vitis vinifera linn. and its conversion to several terpenic natural products of plant and marine origin
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The four-step synthesis of 4-(2,3,6-trimethylphenyl)butan-2-ol (1), starts from 5,8-dimethyl-3,4-dihydro-2-naphthaldehyde (2).The trimethyldihydronaphthalene (10) obtained from the reduction of 2 is ozonised to the keto aldehyde (11), which is reduced to
- Sudalai, A.,Rao, Krishna G. S.
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p. 110 - 112
(2007/10/02)
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- 3-OXO-α-IONOL, VOMIFOLIOL AND ROSEOSIDE IN VITIS VINIFERA FRUIT
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Key Word Index - Vitis vinifera; Vitaceae; grapes; 3-oxo-α-ionol; vomifoliol; dehydrovomifoliol; roseoside; hydrolytic studies. 3-Oxo-α-ionol, vomifoliol and dehydrovomifoliol were identified for the first time in fruit from Vitis vinifera.The last named compound was mainly present free in the juice while the others existed predominantly as conjugates.In the case of vomifoliol, the conjugation was with glucose, i.e. as roseoside.Hydrolytic studies on 3-oxo-α-ionol and vomifoliol gave a range of compounds which have been recognized as fruit and plant products.
- Strauss, Christopher R.,Wilson, Bevan,Williams, Patrick J.
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p. 1995 - 1998
(2007/10/02)
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