- Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: Efficient construction of γ,δ-unsaturated ketones
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A highly regioselective protocol for the direct synthesis of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols was proposed and accomplished relying on the combination of [Ir(cod)Cl]2 and 10-camphorsulfonic acid via decarboxylative allylation.
- Chen, Shu-Jie,Lu, Guo-Ping,Cai, Chun
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p. 11512 - 11514
(2016/01/15)
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- Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl
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The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading.
- Takanami, Toshikatsu,Hayashi, Mikiko,Iso, Kazuhiro,Nakamoto, Hirose,Suda, Kohji
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p. 9467 - 9474
(2007/10/03)
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- Carbon-carbon bond formation by reactions of allylic alcohol with enoxysilane in the presence of Ir-complex
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Substitution of allylic alcohols to form a carbon-carbon bond is accomplished by a simple reaction of the allylic alcohol itself with an enoxysilane, catalyzed by [Ir(cod)(PPh3)2]X which is activated by H2 molecule. The anion part X of the complexes plays an important role to enhance the rate and product yields of the reactions. The efficacy of the catalyst increases with switching X in the order of PF6-4--.
- Matsuda, Isamu,Wakamatsu, Shogo,Komori, Ken-Ichi,Makino, Tatsuya,Itoh, Kenji
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p. 1043 - 1046
(2007/10/03)
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- Rhodium-catalyzed substitution of allylic carbonates with enoxysilanes
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Substitution at the allylic position proceeds smoothly in rhodium-catalyzed reactions of allyl carbonates with enoxysilanes under almost neutral conditions to give γ,δ-unsaturated ketones in good to excellent yields. (C) 2000 Elsevier Science Ltd.
- Muraoka,Matsuda,Itoh
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p. 8807 - 8811
(2007/10/03)
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- Molybdenum(II)- and tungsten(II)-catalyzed allylic substitution
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The molybdenum(II) complexes Mo(CO)5(OTf)2 (7a), [Mo(CO)4Br2]2 (8a), their tungsten(II) congeners 7b and 8b, and bimetallic complex Mo(CO)3(MeCN)2(SnCl3)Cl (9a) have been found to catalyze the C-C bond-forming allylic substitution with silyl enol ethers derived from β-dicarbonyls (e.g., 16 + 30 → 46) or from simple ketones (e.g., 16 + 32 → 50), aldehydes, and esters as nucleophiles under mild conditions (room temperature, 1-2 h). Methanol, as a prototype oxygen nucleophile, reacts in a similar fashion (e.g., 16 + MeOH → 43). Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.
- Malkov, Andrei V.,Baxendale, Ian R.,Dvorak, Dalimil,Mansfield, Darren J.,Kocovsky, Pavel
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p. 2737 - 2750
(2007/10/03)
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- AN EFFECTIVE ACTIVATION OF ALLYL METHYL ETHERS BY A CATALYTIC AMOUNT OF TRITYL PERCHLORATE IN THE ALLYLATION OF SILYL ENOL ETHERS
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In the presence of a catalytic amount of trityl perchlorate, secondary and tertiary allyl methyl ethers smoothly react with silyl enol ethers to afford the corresponding γ,δ-unsaturated carbonyl compounds in good yields.By the combination of this reaction
- Mukaiyama, Teruaki,Nagaoka, Hitoshi,Ohshima, Masahiro,Murakami, Masahiro
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p. 1009 - 1012
(2007/10/02)
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