Sequential Amphiphilic Allylation of Aldimines with 2-Methylenepropane-1,3-diols

The combination of Pd catalyst and triethylborane promotes amphiphilic allylation of aldimine with 2-methylenepropane-1,3-diol in the order of nucleophilic-electrophilic attack to provide pyrrolidine under mild conditions.Nagasaki Symposium on Nano-Dynamics 2008 (NSND2008) 平成20年1月29日(火)於長崎大学 Poster Presentatio

Pd-Catalyzed Nucleophilic Allylation of Carbonyls with 1,3-Dienes

In the presence of Pd catalyst and triethylborane, aldehyde undergoes nucleophilic allylation with butadiene to provide dienyl homoallyl alcohols via bis-π-allylpalldium. The reaction feature depends on the kind of ligands; n-Bu3P promotes two molecules of aldehyeds to react with bis-π-allylpalldium and produces symmetrical dienyl diols, whereas bidentate ligands, dppf and dppe, provide dienyl homoallyl alcohols.Nagasaki Symposium on Nano-Dynamics 2008 (NSND2008) 平成20年1月29日(火)於長崎大学 Poster Presentatio

Ni-Catalyzed Multi-Component Coupling Reaction of Aldimine,1,3-Diene, Alkyne, and Organozinc

Aldimines composed of aldehydes and primary amines react with 1,3-diene,alkyne, and Me_2Zn to furnish dienyl homoallylamines in the presence of Ni catalyst.In case of Ph_2Zn, alkyne serves as a spectator ligand to promote the three-component coupling reaction of Ph_2Zn, diene, and aldimine.Nagasaki Symposium on Nano-Dynamics 2008 (NSND2008) 平成20年1月29日(火)於長崎大学 Poster Presentatio

Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes

Pd-Et3B catalytic system promotes the generation of allyl cations, allyl anions, and zwitterionic trimethylenemethane species from the corresponding allylic alcohols. Allyl cations react with a wide variety of nucleophiles, e.g., amines, active methylene compounds, 1,3,5-trihydroxybenzene, indoles, aldehydes (at the alpha;-position). The reaction is extended to dehydrative Grob fragmentation of 1,3-diols. Allyl anions react with aldimines to give homoallyl amines. Zwitterionic trimethylenemethane, generated from 2-mefhylene-1,3-propanediol, reacts with aldehydes and aldimines to provide 3-methylenecyclopentanols and 3-methylenepyrrolidines, respectively. Vinyl epoxide can be utilized as a synthetic equivalent of 3-butenyl 2-anion-1-cation

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京都大学0048新制・課程博士工学博士甲第1404号工博第345号新制||工||258(附属図書館)3706UT51-48-J42京都大学大学院工学研究科合成化学専攻(主査)教授 吉田 善一, 教授 松浦 輝男, 教授 庄野 達哉学位規則第5条第1項該当Kyoto UniversityDA

Amphiphilic Allylic Alkylation with Allyl Alcohols Promoted by Pd-Catalyst and Triethylborane

The combination of Pd catalyst and triethylborane induces allylic alcohols to undergo direct electrophilic allylation of soft nucleophiles. Similar conditions also accelerate nucleophilic allylations of aldehydes and aldimines to provide homoallyl alcohols and homoallylamines, respectively. Moreover, 2-methylenepropane-1,3-diol undergoes a sequential amphiphilic activation to react with aldehydes and aldimines, giving rise to 3-methylenecyclopentanols and 3-methylenepyrrolidines