Synthesis of chiral quaternary ammonium polymers and their application to asymmetric reaction

手性季铵聚合物的合成及其在不对称反应中的应用

• 批准号: 19550122
• 负责人: ITSUNO Shinichi
• 金额: $ 2.91万
• 依托单位: Toyohashi University of Technology
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2007
• 资助国家: 日本
• 起止时间: 2007 至 2009
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-19550122/
• 关键词: 光学活性高分子; 第四級アンモニウム塩; ジアミン; ジハライド; 高分子不斉触媒; 不斉アルキル化反応; キラル第四級アンモニウム塩; シンコナアルカロイド; キラルジアミン; キラルジハライド; 四級化

Although a substantial amount of work has been carried out using a side chain functionalized polymers, only a limited number of investigations have been performed to elucidate the use of main-chain functional polymers. The main-chain chiral polymer catalysts having rigid and sterically regular structure may have a better defined microenvironment at the catalytic sites and have allowed a systematic modification of their catalytic properties. We have synthesized two different types of chiral main-chain polymers containing quaternary ammonium salt structure. These chiral polymers were used as catalyst for asymmetric alkylation reaction of N-diphenylmethylidene glycine tert-butyl ester to give phenylalanine derivative in high level of enantioselectivity.

尽管使用侧链功能化聚合物进行了大量工作，但仅进行了有限的研究以阐明主链功能聚合物的使用。具有刚性且定期定期结构的主链手性聚合物催化剂在催化位点可能具有更好的定义微环境，并允许系统地修饰其催化性能。我们已经合成了两种不同类型的手性主链聚合物，这些聚合物含有Quaternary铵盐结构。这些手性聚合物被用作N-二苯基甲基甲基甘氨酸TERT叔丁基酯不对称烷基化反应的催化剂，以高水平的对映选择性给予苯丙氨酸衍生物。

项目成果

Immobilization Method of Chiral Catalysts onto Amphiphilic Polymer Supports

• DOI: 10.5059/yukigoseikyokaishi.67.1025
• 发表时间: 2009
• 期刊: Journal of Synthetic Organic Chemistry Japan
• 影响因子: 0.2
• 作者: S. Itsuno

Development of biomedical porous titanium filled with medical polymer by in-situ polymerization of monomer solution infiltrated into pores

• DOI: 10.1016/j.jmbbm.2009.03.003
• 发表时间: 2010-01-01
• 期刊: JOURNAL OF THE MECHANICAL BEHAVIOR OF BIOMEDICAL MATERIALS
• 影响因子: 3.9
• 作者: Nakai, Masaaki;Niinomi, Mitsuo;Shindoh, Taku
• 通讯作者: Shindoh, Taku

Preparation of Chiral Polymers Containing Quaternary Ammonium Sulfonate Structure and Their Use as Catalyst for Asymmetric Reactions

含季铵磺酸盐结构手性聚合物的制备及其作为不对称反应催化剂的应用

• 发表时间: 2009
• 作者: Rimiko Ozawa;Takeshi Hashimoto;Akiyo Yamauchi;Iwao Suzuki Bradly D. Smith;and Takashi Hayashita;伊津野真一
• 通讯作者: 伊津野真一

Polymer-immobilized catalyst for asymmetric hydrogenation of racemic a-(N-benzoyl-N-methylamino) propiophenone

用于外消旋α-(N-苯甲酰基-N-甲氨基)苯丙酮不对称氢化的聚合物固定化催化剂

• 发表时间: 2009
• 期刊: J.Org.Chem. 74
• 作者: Chiwara;V.I.;Haraguchi;N.;Itsuno;S.
• 通讯作者: S.

Preparation of a Polymer-supported 1, 2-Diamine and Its Application to the Asymmetric Hydrogenation of Aromatic Ketones

聚合物负载1, 2-二胺的制备及其在芳香酮不对称加氢中的应用

• 发表时间: 2008
• 期刊: Tetrahedron Asymmetry 19
• 作者: Takahashi;M.;Haraguchi;N.;Itsuno;S.
• 通讯作者: S.