Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (S)-(-)-3-Butylphthalide
文献类型：期刊论文
| 作者 | Zhang, Haoyi1; Zhang, Shilei1,3; Liu, Lu1; Luo, Guangshun1; Duan, Wenhu1,2 ; Wang, Wei1,2,3
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2010-01-15 |
| 卷号 | 75期号:2页码:368-374 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/jo902118x |
| 文献子类 | Review |
| 英文摘要 | The development of efficient methods for the facile construction of important molecular frameworks is an important goal in organic synthesis. Chiral 3-substituted phthalides are widely distributed in it large collection of natural products with broad, potent, and potentially path-pointing biological activities. In this investigation, we have uncovered all unprecedented organocatalytic asymmetric aldol-lactonization reaction of 2-formylbenzoic esters with ketones/aldehydes for convenient construction of the enantioenriched "privileged" scaffold. As a result of the sensitive nature Of Substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst L-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO(2)H can significantly enhance reaction efficiency with use of only as low as 2.5 mol % IV for the process. Moreover, due to the sensitivity of reaction conditions toward it sequential aldol-lactonization process without affecting enantioselectivity and racemization, it is essential to remove the catalyst for the subsequent facile lactonization reaction in the presence of K(2)CO(3). The aldol-lactonization processes serve as it powerful approach to the preparation of synthetically and biologically important 3-substitued phthalides with a high level of enantioselectivities. A 3-step catalytic asymmetric synthesis of the natural product of 3-butylphthalide is reported. |
| WOS关键词 | CATALYTIC ASYMMETRIC ALDOL ; DIPHENYLPROLINOL SILYL ETHER ; OPTICALLY-ACTIVE PHTHALIDES ; SECONDARY MOLD METABOLITES ; MICHAEL ADDITION-REACTIONS ; HIGHLY EFFICIENT CATALYST ; ONE-POT SYNTHESIS ; ALPHA,BETA-UNSATURATED ALDEHYDES ; TRANSFER HYDROGENATION ; CARBONYL-COMPOUNDS |
| 资助项目 | Pharmacy, East China University of Science and Technology[00000000] ; China 111 Project[B07023] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000273400300011 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278994]  |
| 专题 | 药理学第二研究室 |
| 通讯作者 | Wang, Wei |
| 作者单位 | 1.E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Sci, Shanghai 200237, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China; 3.Univ New Mexico, Dept Chem & Biol Chem, Albuquerque, NM 87131 USA |
| 推荐引用方式 GB/T 7714 | Zhang, Haoyi,Zhang, Shilei,Liu, Lu,et al. Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (S)-(-)-3-Butylphthalide[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(2):368-374. |
| APA | Zhang, Haoyi,Zhang, Shilei,Liu, Lu,Luo, Guangshun,Duan, Wenhu,&Wang, Wei.(2010).Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (S)-(-)-3-Butylphthalide.JOURNAL OF ORGANIC CHEMISTRY,75(2),368-374. |
| MLA | Zhang, Haoyi,et al."Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (S)-(-)-3-Butylphthalide".JOURNAL OF ORGANIC CHEMISTRY 75.2(2010):368-374. |
入库方式： OAI收割
来源：上海药物研究所
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