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9 results on '"retro-allylation"'

1. Synthetic Application of Intramolecular Cyanoboration on the Basis of Removal and Conversion of a Tethering Group by Palladium-Catalyzed Retro-Allylation.

Author

Ohmura, Toshimichi, Awano, Tomotsugu, Suginome, Michinori, Yorimitsu, Hideki, and Oshima, Koichiro

Subjects
*ALLYLATION, *PALLADIUM catalysts, *ARYLATION kinetics, *NITRILE derivatives, *ALKENES, *HYDROCARBONS spectra
Abstract

A new synthetic strategy, involving utilization of a tethered intramolecular reaction with a removable tether, was demonstrated by the intramolecular cyanoboration-retro-allylation sequence. [ABSTRACT FROM AUTHOR]

Published
2008
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2. Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction

Author

Hayashi, Sayuri, Hirano, Koji, Yorimitsu, Hideki, and Oshima, Koichiro

Subjects
*GRIGNARD reagents, *GALLIUM compounds, *ALCOHOLS (Chemical class), *CHEMICAL reactions
Abstract

Abstract: A new method for the preparation and control of dynamic σ-allylgalliums is disclosed. Upon treatment with a Grignard reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined crotylgallium reagents effected stereoselective allylation of aldehydes. Allylgallation reaction of alkynes with the allylgallium reagents prepared by retro-allylation is also described. [Copyright &y& Elsevier]

Published
2007
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3. Rhodium-catalyzed allyl transfer from homoallyl alcohols to acrylate esters via retro-allylation

Author

Jang, Minsul, Hayashi, Sayuri, Hirano, Koji, Yorimitsu, Hideki, and Oshima, Koichiro

Subjects
*ALLYL chloride, *ALCOHOLS (Chemical class), *ACRYLATES, *ESTERS
Abstract

Abstract: Retro-allylation of homoallyl alcohols by rhodium catalysts occurs to generate allylrhodium species. Insertion of acrylate esters to the allylrhodiums proceeds to give the corresponding 2,5-hexadienoate esters in situ. Subsequent isomerization or iterative 1,4-addition takes place in the same pots to furnish the corresponding 2,4-hexadienoate esters or triesters in good yields. [Copyright &y& Elsevier]

Published
2007
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4. Synthetic Application of Intramolecular Cyanoboration on the Basis of Removal and Conversion of a Tethering Group by Palladium-Catalyzed Retro-Allylation

Author

Hideki Yorimitsu, Tomotsugu Awano, Koichiro Oshima, Michinori Suginome, and Toshimichi Ohmura

Subjects
endocrine system, alkenes, Intramolecular reaction, Chemistry, Stereochemistry, Tethering, organic chemicals, Organic Chemistry, food and beverages, chemistry.chemical_element, Sequence (biology), palladium, Combinatorial chemistry, Catalysis, nitrites, retro-allylation, Intramolecular force, nitriles, arylation, Palladium
Abstract

A new synthetic strategy, involving utilization of a tethered intramolecular reaction with a removable tether, was demonstrated by the intramolecular cyanoboration-retro-allylation sequence.

Published
2008
Full Text
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6. Rhodium-catalyzed allyl transfer from homoallyl alcohols to acrylate esters via retro-allylation

Author

Hideki Yorimitsu, Koji Hirano, Minsul Jang, Koichiro Oshima, and Sayuri Hayashi

Subjects
Acrylate, Organic Chemistry, chemistry.chemical_element, General Medicine, Biochemistry, allyl transfer, Rhodium, Catalysis, allylrhodium, chemistry.chemical_compound, retro-allylation, chemistry, carbon-carbon bond cleavage, Polymer chemistry, Drug Discovery, Organic chemistry, Isomerization
Abstract

Retro-allylation of homoallyl alcohols by rhodium catalysts occurs to generate allylrhodium species. Insertion of acrylate esters to the allylrhodiums proceeds to give the corresponding 2,5-hexadienoate esters in situ. Subsequent isomerization or iterative 1,4-addition takes place in the same pots to furnish the corresponding 2,4-hexadienoate esters or triesters in good yields.

Published
2007
Full Text
View/download PDF

7. Synthetic Application of Intramolecular Cyanoboration on the Basis of Removal and Conversion of a Tethering Group by Palladium-Catalyzed Retro-Allylation

Author

00378803, 60252483, 00372566, 00111922, Ohmura, Toshimichi, Awano, Tomotsugu, Suginome, Michinori, Yorimitsu, Hideki, Oshima, Koichiro, 00378803, 60252483, 00372566, 00111922, Ohmura, Toshimichi, Awano, Tomotsugu, Suginome, Michinori, Yorimitsu, Hideki, and Oshima, Koichiro

Abstract

A new synthetic strategy, involving utilization of a tethered intramolecular reaction with a removable tether, was demonstrated by the intramolecular cyanoboration-retro-allylation sequence.

Published
2008

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