Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines
文献类型：期刊论文
| 作者 | Li, Yi1; Xu, Ming-Hua1,2,3
|
| 刊名 | ACTA CHIMICA SINICA
 |
| 出版日期 | 2021-11-15 |
| 卷号 | 79期号:11页码:1345-1359 |
| 关键词 | Petasis reaction chiral amine boronic acid asymmetric synthesis asymmetric catalysis |
| ISSN号 | 0567-7351 |
| DOI | 10.6023/A21080391 |
| 通讯作者 | Xu, Ming-Hua(xumh@sustech.edu.cn) |
| 英文摘要 | Chiral amines are valuable constituents of many natural products, pharmaceuticals and functional materials, they are also widely utilized as versatile building blocks and important chiral catalysts as well as chiral auxiliaries in organic synthesis. Therefore, it is of great scientific significance and application value to develop efficient methods for the synthesis of structurally diverse chiral amines and chiral amine scaffolds. In 1993, Petasis and co-workers reported an efficient synthesis of allylic amines through a Mannich-type reaction of vinylboronic acids with secondary amines and paraformaldehyde, where the organoboron reagents served as the nucleophilic component. Since then, this three-component Petasis reaction of organoboron reagents with amines and carbonyl derivatives has been developed as an appealing and concise method to access various amines. The asymmetric Petasis reaction provides a facile and efficient route to optically active amines and thus has attracted much attention over the past two decades. In this review, we summarize the recent progress achieved in the synthesis of chiral amines by asymmetric Petasis reaction and provide an overview on the methods applied for stereochemical control. The strategies that have been employed for accessing enantioenriched amines, including various chiral substrate-based diastereoselective induction approaches and several recent developments of enantioselective catalysis. In a large number of asymmetric Petasis reaction cases, good to high levels of stereoselectivities can be achieved relying on the utilization of chiral amine source, chiral carbonyl substrates, and chiral organoboron reagents. In particular, chiral amines such as a-methylbenzylamines and chiral a-hydroxy aldehyde analogues have emerged as a broadly applicable class of substrates for asymmetric Petasis reaction. The most promising advance has been the success of catalytic asymmetric Petasis reaction for enantioselective synthesis of chiral amines in the last few years. Chiral bifunctional thioureas and binaphthols have been demonstrated to be effective organocatalysts. Finally, the perspectives on the relevant challenges and future directions in this field are also discussed. |
| WOS关键词 | BORONO-MANNICH REACTION ; STEREOSELECTIVE-SYNTHESIS ; 3-COMPONENT REACTION ; BIS(SULFINYL)IMIDOAMIDINE LIGANDS ; BUILD/COUPLE/PAIR STRATEGY ; EFFICIENT SYNTHESIS ; LEGIONAMINIC ACID ; ENANTIOPURE ; HYDROGENATION ; DERIVATIVES |
| 资助项目 | National Natural Science Foundation of China[21971103] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000716442000004 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/298958]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Xu, Ming-Hua |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China 3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Dept Chem, Shenzhen 518055, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Yi,Xu, Ming-Hua. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines[J]. ACTA CHIMICA SINICA,2021,79(11):1345-1359. |
| APA | Li, Yi,&Xu, Ming-Hua.(2021).Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines.ACTA CHIMICA SINICA,79(11),1345-1359. |
| MLA | Li, Yi,et al."Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines".ACTA CHIMICA SINICA 79.11(2021):1345-1359. |
入库方式： OAI收割
来源：上海药物研究所
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