Development of highly efficient asymmetric synthesis process using simple five-membered heterocycles

使用简单五元杂环开发高效不对称合成工艺

• 批准号: 17590010
• 负责人: MATSUNAGA Hirofumi
• 金额: $ 2.3万
• 依托单位: Kumamoto University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2005
• 资助国家: 日本
• 起止时间: 2005 至 2006
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-17590010/
• 关键词: roofed; asymmetric synthesis; 1,2-diamines; asymmetric alkylation; asymmetric transfer hydrogenation; iminothioether; asymmetric Diels-Alder reaction; 2-thiazoline; 不斉置換変換反応; イミノジスルフィド; 2-アミノチオール; アリールイミン

The aim of this research is to establish the methodology for excellent asymmetric reactions using bicyclic "roofed" 2-airino alcohols, 1,2-diamines and 2-aminothiols and their derivatives, derived from the corresponding tricyclic 2-oxazolidinones, 2-imidazolidinones and 2-thiazolidinones, and they have been proven to be good to excellent chiral ligands for following metal-catalyzed asymmetric reactions:1) "Roofed" 2-iminothioether-Pd (II) complex-catalyzed asymmetric substitution (alkylation, amination) of allylacetates.2) "Roofed"2-thiazoline-Cu (II) complex-catalyzed asymmetric Diels-Alder reaction.3) "Roofed" cis-1,2-diamine-Ru (II) complex-catalyzed asymmetric transfer hydrogenation of ketones and imines.

本研究的目的是建立一种利用双环“屋顶”的2-氨基醇、1，2-二胺和2-氨基硫醇及其衍生物进行不对称反应的方法，这些衍生物是由相应的三环2-恶唑烷酮、2-咪唑烷酮和2-噻唑烷酮衍生的，它们已被证明是以下金属催化的不对称反应的良好手性配体：1）“Roofed”2-亚胺硫醚-Pd（II）配合物催化的乙酸烯丙酯的不对称取代（烷基化、胺化）; 2）“Roofed“2-噻唑啉-Cu（II）配合物催化的不对称Diels-Alder反应; 3）“Roofed”cis-1，2-diamine-Ru（II）配合物催化的酮和亚胺的不对称转移氢化。

项目成果

Sterically congested "roofed" 2-iminothioethers as new chiral ligands for palladium-catalyzed asymmetric allylic alkylation

• DOI: 10.3987/com-05-s(k)50
• 发表时间: 2005-12
• 期刊: Heterocycles
• 影响因子: 0.6
• 作者: Ryoh Tokuda;H. Matsunaga;T. Ishizuka;M. Nakajima;T. Kunieda

Sterically Congested "Roofed" 2-Thiazolines as New Chiral Ligands for Copper(II)-Catalyzed Asymmetric Diels-Alder Reactions

空间拥挤的“屋顶”2-噻唑啉作为铜(II)催化不对称狄尔斯-阿尔德反应的新手性配体

• 发表时间: 2005
• 期刊: Tetrahedron Letters 46
• 作者: Yamakuchi;M.
• 通讯作者: M.

Asymmetric ring opening of meso-epoxides catalyzed by the chiral phosphine oxide BINAPO

• DOI: 10.1016/j.tetasy.2005.06.021
• 发表时间: 2005-07-18
• 期刊: TETRAHEDRON-ASYMMETRY
• 作者: Tokuoka, E;Kotani, S;Nakajima, M
• 通讯作者: Nakajima, M

Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex

手性“屋顶”顺式二胺-Ru(II)络合物催化酮的高效不对称转移氢化

• 发表时间: 2005
• 期刊: Tetrahedron Letters 46
• 作者: Matsunaga;H. et al.
• 通讯作者: H. et al.