Development of the Catalytic Asymmetric Tandem Reactions

催化不对称串联反应的进展

• 批准号: 11672112
• 负责人: IKEDA Shin-ichi
• 金额: $ 1.6万
• 依托单位: Nagoya City University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1999
• 资助国家: 日本
• 起止时间: 1999 至 2000
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-11672112/
• 关键词: tandem reaction; enantioselectivity; oxazoline; cyclotrimerization; エナンチス選択的; 単座オキサゾリン配位子

We have found a nickel-catalyzed asymmetric multiple-component coupling of enones, alkynes, dimethylzinc, and chlorotrimethylsilane. Interestingly, catalytic systems involving simple monodentate chiral oxazolines, which have been previously used as valuable chiral auxiliaries, were very effective in giving optically active coupling products. In contrast some optically active organophosphorus ligands and bidentate oxazolines, which have been extensively used as ligands for transition metals in asymmetric catalysis, did not give enantioselection. Moreover, we have found an asymmetric cyclotrimerization of enones and alkynes in the presence of a catalytic system of nickel and aluminum. The chiral monooxazoline ligands were also effective in the reaction.

我们已经发现了一个镍催化的不对称多组分偶联的烯酮，炔，二甲基锌，氯三甲基硅烷。有趣的是，催化体系涉及简单的单齿手性恶唑啉，这以前已被用作有价值的手性助剂，是非常有效的光学活性耦合产品。而在不对称催化反应中被广泛用作过渡金属配体的一些光学活性有机磷配体和双齿恶唑啉配体则不具有对映选择性。此外，我们还发现了在镍和铝催化体系存在下烯酮和炔的不对称环三聚反应。手性单恶唑啉配体在反应中也是有效的。

项目成果

池田慎一: "ニッケル触媒を用いた高選択的多成分連結反応の開発"化学と工業. 53・2. 146-149 (2000)

池田真一：“使用镍催化剂的高选择性多组分偶联反应的开发”化学与工业 146-149（2000）。

Shin-ichi Ikeda: "Nickel-Catalyzed Intermolecular Domino Reaction"Accounts of Chemical Research. 33. 511-519 (2000)

Shin-ichi Ikeda：“镍催化分子间多米诺反应”化学研究记述。

池田慎一: "ニッケル触媒を用いた高選択的多成分連結反応の開発"化学と工業. 53. 146-149 (2000)

Shinichi Ikeda：“使用镍催化剂开发高选择性多组分偶联反应”化学与工业 53. 146-149 (2000)。

Shin-ichi Ikeda: "Nickel-Catalyzed Intermolecular Domino Reactions"Acc.Chem.Res.. 33. 511-519 (2000)

Shin-ichi Ikeda：“镍催化的分子间多米诺反应”Acc.Chem.Res. 33. 511-519 (2000)

Shin-ichi Ikeda: "Nickel-Cutalyzed Asymmetric Multiple-Component Tandem Coupling. Effects of Simple Monodentate Oxazolines as Chiral Ligands"Journal of the American Chemical Society. 121・19. 4712-4713 (1999)

Shin-ichi Ikeda：“镍切割不对称多组分串联偶联。简单单齿恶唑啉作为手性配体的影响”美国化学会杂志 121・19（1999）。