Asymmetric Addition of carbon, nitrogen, oxygen and sulfur nucleophiles and its application to the synthesis of biologically active compounds

碳、氮、氧、硫亲核试剂的不对称加成及其在生物活性化合物合成中的应用

• 批准号: 20249002
• 负责人: TOMIOKA Kiyoshi
• 金额: $ 24.29万
• 依托单位: Doshisha Women's College of Liberal Arts (2011)Kyoto University (2008-2010)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (A)
• 财政年份: 2008
• 资助国家: 日本
• 起止时间: 2008 至 2011
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-20249002/
• 关键词: 四大元素; キラル配位子; 不斉触媒; 天然物合成; 連続反応

Most chiral carbon centers of biologically active compound directly connect to representative 4 atoms, carbon, nitrogen, oxygen, and sulfur atoms. Asymmetric addition reaction of these 4 atoms develops the methodology for the efficient synthesis of useful medicines and biologically active molecules. We achieved asymmetric addition of organolithiums, lithium enolates, lithium amides, organoboranes, organomagnesiums, and organozincs. Asymmetric total synthesis of some natural products was also achieved by using our developed asymmetric reaction as a key step.

大多数生物活性化合物的手性碳中心直接连接至代表性的4个原子：碳、氮、氧和硫原子。这 4 个原子的不对称加成反应开发了有效合成有用药物和生物活性分子的方法。我们实现了有机锂、烯醇锂、氨基锂、有机硼烷、有机镁和有机锌的不对称加成。以我们开发的不对称反应为关键步骤，还实现了一些天然产物的不对称全合成。

项目成果

Aminolithiation. Carbolithiation Conjugate Process

氨基锂化。

• 发表时间: 2011
• 作者: Tomioka;K.
• 通讯作者: K.

Asymmetric construction of quaternary carbon centers by sequential conjugate addition of lithium amide and in situ alkylation: utility in the synthesis of (-)-aspidospermidine.

• DOI: 10.1021/ol802759j
• 发表时间: 2009-02
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: Mayuko Suzuki;Y. Kawamoto;Takeo Sakai;Y. Yamamoto;K. Tomioka

Stereoselective Radical Addition of an Acetal to Sterically Tuned Enantiomerically Pure N-Sulfinyl Imines

缩醛与空间调节的对映体纯 N-亚磺酰亚胺的立体选择性自由基加成

• 发表时间: 2010
• 期刊: Chem.Pharm.Bull. 58
• 作者: K.Tomioka;K.Tomioka
• 通讯作者: K.Tomioka

Chiral N-Heterocyclic Carbene. Copper(I)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides : Steric and Electronic Effects on γ-Selectivity

手性 N-杂环卡宾。铜 (I) 催化的脂肪族烯丙基溴化物的不对称烯丙基化：对 γ 选择性的空间和电子效应

• DOI: 10.1021/jo102386s
• 发表时间: 2011
• 期刊: J. Org. Chem
• 作者: Selim;K. B.; Nakanishi;H.; Matsumoto;Y.; Yamamoto;Y.; Yamada;K.; Tomioka;K
• 通讯作者: K

Hydroamination of Carbon-Carbon Double Bond for Nitrogen-Containing Heterocycle

含氮杂环碳-碳双键加氢胺化

• 发表时间: 2008
• 作者: Tomioka;K.;富岡清;K.Tomioka
• 通讯作者: K.Tomioka