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Luiz F Silva - One of the best experts on this subject based on the ideXlab platform.
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Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.
Organic Letters, 2007Co-Authors: Luiz F Silva, Fernanda A. Siqueira, Eliane C. Pedrozo, Fabiana Y. M. Vieira, Antonio C. DoriguettoAbstract:A new approach for the synthesis of (±)-indatraline, which is a 3-phenyl-1-Indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the Indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain Indans.
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Rearrangement of Homoallylic Alcohols with Thallium(III): Diastereoselective Synthesis of Indans Bearing a β-Hydroxy Ketone Moiety
Synthesis, 2007Co-Authors: Luiz F Silva, Fabiana Y. M. Vieira, Samir A. P. Quintiliano, Marcus V. Craveiro, Helena M. C. FerrazAbstract:Several aspects of the synthesis of Indans through a thallium(III)-mediated ring contraction reaction of 1,2-dihydronaphthalene derivatives bearing suitably positioned primary and secondary hydroxyl groups are disclosed. The relative configuration of 3-(2,3-dihydro-1 1H-inden-3-yl)-2-methyl-3-oxopropyl 4-bromobenzoate was assigned by X-ray crystal structure analysis, allowing additional insights into the mechanism of the thallium(III)-promoted oxidative rearrangement ofhomoallylic alcohols. The reaction of primary homoallylic alcohols bearing the electron-withdrawing group bromine gave Indans in 52-55% yield using an excess of thallium tri-nitrate (TTN). Furthermore, the thallium(III)-mediated oxidative rearrangement of the secondary homoallylic alcohols gave, in a diastereoselective fashion, Indans bearing up to three stereocenters.
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Rearrangement of beta,gamma-unsaturated esters with thallium trinitrate: synthesis of Indans bearing a beta-keto ester moiety
Journal of the Brazilian Chemical Society, 2006Co-Authors: Luiz F Silva, Eliane C. Pedrozo, Helena M. C. FerrazAbstract:The rearrangement of b,g-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl)-propionic acid ethyl ester, with thallium trinitrate (TTN) in acetic acid leads to 3-Indan-1-yl-2-methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new Indans thus obtained feature a b-keto ester moiety, which would be useful for further functionalization.
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γ γ-Unsaturated Esters with Thallium Trinitrate: Synthesis of Indans Bearing a β-Keto Ester Moiety
2006Co-Authors: Luiz F Silva, Eliane C. Pedrozo, Helena M. C. FerrazAbstract:O rearranjo de esteres β,γ-insaturados, tais como 2-(3,4-di-hidronaftalen-1-il)-propionato de etila, com trinitrato de talio (TTN) em acido acetico leva a 3-Indan-1-il-2-metil-3-oxopropionatos de etila com bom rendimento, atraves de uma reacao de contracao de anel. Os novos Indanos assim obtidos possuem uma unidade β-ceto ester, a qual pode ser util para transformacoes posteriores. The rearrangement of β,γ-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl)propionic acid ethyl ester, with thallium trinitrate (TTN) in acetic acid leads to 3-Indan-1-yl-2methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new Indans thus obtained feature a β-keto ester moiety, which would be useful for further functionalization.
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Model Studies Toward the Synthesis of Natural Indans Utilizing a Thallium(III)-Mediated Ring-Contraction Reaction
Synthesis, 2003Co-Authors: Helena M. C. Ferraz, Andrea M. Aguilar, Luiz F SilvaAbstract:6-Methoxy-1-tetralone was transformed in six steps into an Indan derivative related to the sesquiterpenes mutisianthol and jungianol. Key steps involve a thalium(III)-promoted ring-contraction (to assemble the Indan unit)and a Wittig olefination (to attach the side chain).
Helena M. C. Ferraz - One of the best experts on this subject based on the ideXlab platform.
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Rearrangement of Homoallylic Alcohols with Thallium(III): Diastereoselective Synthesis of Indans Bearing a β-Hydroxy Ketone Moiety
Synthesis, 2007Co-Authors: Luiz F Silva, Fabiana Y. M. Vieira, Samir A. P. Quintiliano, Marcus V. Craveiro, Helena M. C. FerrazAbstract:Several aspects of the synthesis of Indans through a thallium(III)-mediated ring contraction reaction of 1,2-dihydronaphthalene derivatives bearing suitably positioned primary and secondary hydroxyl groups are disclosed. The relative configuration of 3-(2,3-dihydro-1 1H-inden-3-yl)-2-methyl-3-oxopropyl 4-bromobenzoate was assigned by X-ray crystal structure analysis, allowing additional insights into the mechanism of the thallium(III)-promoted oxidative rearrangement ofhomoallylic alcohols. The reaction of primary homoallylic alcohols bearing the electron-withdrawing group bromine gave Indans in 52-55% yield using an excess of thallium tri-nitrate (TTN). Furthermore, the thallium(III)-mediated oxidative rearrangement of the secondary homoallylic alcohols gave, in a diastereoselective fashion, Indans bearing up to three stereocenters.
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Rearrangement of beta,gamma-unsaturated esters with thallium trinitrate: synthesis of Indans bearing a beta-keto ester moiety
Journal of the Brazilian Chemical Society, 2006Co-Authors: Luiz F Silva, Eliane C. Pedrozo, Helena M. C. FerrazAbstract:The rearrangement of b,g-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl)-propionic acid ethyl ester, with thallium trinitrate (TTN) in acetic acid leads to 3-Indan-1-yl-2-methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new Indans thus obtained feature a b-keto ester moiety, which would be useful for further functionalization.
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γ γ-Unsaturated Esters with Thallium Trinitrate: Synthesis of Indans Bearing a β-Keto Ester Moiety
2006Co-Authors: Luiz F Silva, Eliane C. Pedrozo, Helena M. C. FerrazAbstract:O rearranjo de esteres β,γ-insaturados, tais como 2-(3,4-di-hidronaftalen-1-il)-propionato de etila, com trinitrato de talio (TTN) em acido acetico leva a 3-Indan-1-il-2-metil-3-oxopropionatos de etila com bom rendimento, atraves de uma reacao de contracao de anel. Os novos Indanos assim obtidos possuem uma unidade β-ceto ester, a qual pode ser util para transformacoes posteriores. The rearrangement of β,γ-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl)propionic acid ethyl ester, with thallium trinitrate (TTN) in acetic acid leads to 3-Indan-1-yl-2methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new Indans thus obtained feature a β-keto ester moiety, which would be useful for further functionalization.
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Model Studies Toward the Synthesis of Natural Indans Utilizing a Thallium(III)-Mediated Ring-Contraction Reaction
Synthesis, 2003Co-Authors: Helena M. C. Ferraz, Andrea M. Aguilar, Luiz F SilvaAbstract:6-Methoxy-1-tetralone was transformed in six steps into an Indan derivative related to the sesquiterpenes mutisianthol and jungianol. Key steps involve a thalium(III)-promoted ring-contraction (to assemble the Indan unit)and a Wittig olefination (to attach the side chain).
Hiromichi Fujioka - One of the best experts on this subject based on the ideXlab platform.
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asymmetric synthesis of chiral spirocyclanes a new route to the optically active spiro cyclopentane 1 1 Indan 2 5 dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
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Asymmetric synthesis of chiral spirocyclanes: A new route to the optically active spiro[cyclopentane-1,1′-Indan]-2,5-dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
Yasuyuki Kita - One of the best experts on this subject based on the ideXlab platform.
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asymmetric synthesis of chiral spirocyclanes a new route to the optically active spiro cyclopentane 1 1 Indan 2 5 dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
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Asymmetric synthesis of chiral spirocyclanes: A new route to the optically active spiro[cyclopentane-1,1′-Indan]-2,5-dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
Sachiko Mihara - One of the best experts on this subject based on the ideXlab platform.
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asymmetric synthesis of chiral spirocyclanes a new route to the optically active spiro cyclopentane 1 1 Indan 2 5 dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
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Asymmetric synthesis of chiral spirocyclanes: A new route to the optically active spiro[cyclopentane-1,1′-Indan]-2,5-dione system
Tetrahedron Letters, 1996Co-Authors: Yasuyuki Kita, Shinji Kitagaki, Reiko Imai, Sachi Okamoto, Sachiko Mihara, Yasushi Yoshida, Shuji Akai, Hiromichi FujiokaAbstract:Abstract A new route to the optically pure spiro[cyclopentane-1,1′-Indan]-2,5-dione system, which is supposed to be valuable for the asymmetric synthesis of optically active fredericamycin A, has been developed through a stereospecific rearrangement of the trans - α , β -epoxy acylates in the tetrahydrobenz[e]Indan systems.
