Development of Advanced Molecular Transformations of Functional Carbon Molecules using Fine Acid-Base Catalysts

使用精细酸碱催化剂开发功能性碳分子的高级分子转化

• 批准号: 17065010
• 负责人: MARUOKA Keiji
• 金额: $ 82.82万
• 依托单位: Kyoto University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research on Priority Areas
• 财政年份: 2005
• 资助国家: 日本
• 起止时间: 2005 至 2008
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-17065010/
• 关键词: 炭素資源; 有機酸塩基触媒; 高度分子変換; プロセス有機合成化学; キラル相間移動反応; 光学活性アミノ酸; 二官能基性有機触媒; キラルジカルボン酸触媒; キラル相間移動触媒; キラル二官能性アミン触媒; 不斉アミノ化反応; 不斉マンニッヒ反応; アルドール反応; キラルジカルボン酸; イミノアザエナミン反応; 炭素炭素結合形成反応; アミノ酸; 不斉共役付加反応; 不斉アルドール反応; 不斉分子変換反応; 二官能基性触媒; 不斉ヒドロキシアミノ化; スピロ

The development of excellent synthetic organic reactions to prepare important materials is urgent to Japan, where natural resources are scarce, as a scientific and technological country in order to keep the international superiority in the field of pharmaceutical and chemical industries. In this priority area, we utilize the readily accessible carbon resources efficiently, and pursuit new carbon-carbon bond-forming reactions based on the truly efficient molecular transformations. Namely, the field of asymmetric phase transfer chemistry, which is regarded as a desirable approach in process synthetic organic chemistry, has been exploited by using chiral binaphthyl-modified quaternary ammonium salts for the development of new, efficient asymmetric carbon-carbon bond-forming reactions. A rational design of chiral bifunctional organocatalysts and chiral dicarboxylic acid catalysts have been also realized for developing several new asymmetric methodologies.

对于自然资源稀缺的日本来说，为了保持在医药和化工领域的国际优势，开发优良的合成有机反应制备重要材料是当务之急。在这一优先领域，我们高效地利用容易获得的碳资源，在真正有效的分子转化的基础上寻求新的碳-碳键形成反应。也就是说，不对称相转移化学被认为是过程合成有机化学中一种理想的方法，通过使用手性联萘修饰的季铵盐来开发新的、高效的不对称碳-碳键形成反应，从而开拓了这一领域。手性双功能有机催化剂和手性二元酸催化剂的合理设计也为开发几种新的不对称方法奠定了基础。

项目成果

Asymmetric imino aza-enamine reaction catalyzed by axially chiral dicarboxylic acid:: Use of arylaldehyde N,N-dialkylhydrazones as acyl anion equivalent

• DOI: 10.1021/ja802704j
• 发表时间: 2008-06-18
• 期刊: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
• 影响因子: 15
• 作者: Hashimoto, Takuya;Hirose, Maya;Maruoka, Keiji
• 通讯作者: Maruoka, Keiji

Design of axially chiral dicarboxylic acid for asymmetric Mannich reaction of arylaldehyde N-Boc imines and diazo compounds

• DOI: 10.1021/ja0713375
• 发表时间: 2007-08-22
• 期刊: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
• 影响因子: 15
• 作者: Hashimoto, Takuya;Maruoka, Keiji
• 通讯作者: Maruoka, Keiji

Highly enantioselective phase-transfer-catalyzed alkylation of protected α-amino acid amides toward practical asymmetric synthesis of vicinal diamines, α-amino ketones, and α-amino alcohols

• DOI: 10.1021/ja0459328
• 发表时间: 2005-04-13
• 期刊: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
• 影响因子: 15
• 作者: Ooi, T;Takeuchi, M;Maruoka, K
• 通讯作者: Maruoka, K

Powerful chiral Phase Transfer Catalysts for the Asymmetric Synthesis of a-Alkyl- and a, a-Dialkyl-a-amino Acids

用于不对称合成α-烷基-和α,α-二烷基-α-氨基酸的强手性相转移催化剂

• 发表时间: 2005
• 期刊: Angewandte Chemie International Edition in English 44
• 作者: Masanori Kitamura

Design of Binaphthyl-Modified Chiral Organocatalysts for Asymmetric Synthesis

用于不对称合成的联萘改性手性有机催化剂的设计

• 发表时间: 2008
• 作者: Maruoka;K.
• 通讯作者: K.