- Remarkable enhancement of photo-allylation of aromatic carbonyl compounds with a hypervalent allylsilicon reagent by donor molecules
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Photo-allylation of various aromatic carbonyl compounds with a penta-coordinated allylsiliconate reagent was remarkably accelerated by the addition of a donor molecule. As the oxidation potential of the allylsiliconate was significantly decreased in the p
- Nishigaichi, Yutaka,Suzuki, Akira,Takuwa, Akio
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Read Online
- Development of a Phase-Transfer-Catalyzed, [2,3]-Wittig Rearrangement
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An investigation into the use of phase-transfer catalysis for the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds is described. Initial studies focused on identifying viable substrate classes that would undergo selective [2,3]-rearrangement under phase-transfer catalysis. Under certain conditions, the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds takes place in the presence of a phase-transfer agent, providing a rare example of a phase-transfer-catalyzed unimolecular reaction. In the course of this investigation, it was found that catalysis is dependent on several variables including base concentration, catalyst structure, and substrate lipophilicity. Preliminary testing of chiral, nonracemic phase-transfer catalysts has shown promising levels of enantioselectivity for future development.
- Denmark, Scott E.,Cullen, Lindsey R.
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p. 11818 - 11848
(2015/12/11)
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- Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents
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Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the react
- Nishigaichi, Yutaka,Orimi, Takayuki,Takuwa, Akio
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experimental part
p. 3837 - 3839
(2010/03/04)
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- Indium-mediated allylation of 1,2-diketones
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Indium-mediated allylation of 1,2-dicarbonyl compounds with indium and allylic bromides was achieved in the presence of nBu4NI or NH4Cl as additive to afford mono- and/or diallylated products in good yields.
- Kang, Suk-Ku,Baik, Tae-Gon,Jiao, Xiang-Hua
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- Regioreversed Allylation in Lewis Acid-mediated and Photochemical Addition Reactions of Unsymmetric α-Diketones with Allylic Stannanes
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In the photochemical reaction of allyl- and benzyltrimethylstannanes with unsymmetric α-diketones (PhCOCOR), the allylic group was introduced to the benzoyl carbon in high or excellent selectivity, whereas the acyl carbon was allylated either exclusively
- Takuwa, Akio,Nishigaichi, Yutaka,Yamashita, Koichi,Iwamoto, Hidetoshi
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p. 1761 - 1764
(2007/10/02)
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- Complete Control of the Rearrangement Modes of Enolates of α-Allyloxy Ketones: Reversal from the -Claisen to the -Wittig Pathway by the Use of the Metalated N,N-Dimethylhydrazones
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It has been shown that the predilection for the -Claisen rearrangement pathway of enolates of α-allyloxy ketones is cleanly overridden by the -Wittig rearrangement route with the use of carboanions of their corresponding N,N-dimethylhydrazones.S
- Luengo, Juan I.,Koreeda, Masato
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p. 5415 - 5417
(2007/10/02)
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