Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions
文献类型：期刊论文
| 作者 | Wang, Qian1; Wang, De-Xian2; Wang, Mei-Xiang3; Zhu, Jieping1 |
| 刊名 | ACCOUNTS OF CHEMICAL RESEARCH
 |
| 出版日期 | 2018-05-01 |
| 卷号 | 51期号:5页码:1290-1300 |
| ISSN号 | 0001-4842 |
| DOI | 10.1021/acs.accounts.8b00105 |
| 英文摘要 | CONSPECTUS: The Passerini three-component (P-3CR) and the Ugi four-component (U-4CR) are two of the most prominent isocyanide-based multicomponent reactions (IMCRs). The P-3CR transforms isocyanides, aldehydes (ketones), and carboxylic acids to a-acyloxy carboxamides, while the U-4CR converts isocyanides, aldehydes (ketones), amines, and carboxylic acids to a-acetamido carboxamides. Conversion of the high energy formal divalent isocyano carbon into a tetravalent amide carbonyl carbon provides the driving force for these reactions. While the prototypical P-3CR and U-4CR provide linear adducts, many heterocycles and macrocycles are now readily synthesized by modifying these truly versatile reactions. As one stereocenter is generated by the nucleophilic addition of the isocyanide to the carbonyl and imine functions, the search for enantioselective versions of these reactions has become a much sought after goal among synthetic chemists. This seemingly trivial endeavor turns out to be extremely difficult to achieve, in sharp contrast to the remarkable progress documented in the field of asymmetric synthesis in general and catalytic enantioselective nucleophilic addition to C=X bond in particular. Since Denmark's first report in 2003 on the catalytic enantioselective Passerini two-component reaction of isocyanides with aldehydes, several Lewis acid (LA) and Bronsted acid-catalyzed enantioselective protocols have been developed. However, it is fair to say that truly catalytic enantioselective P-3CR and U-4CR with wide application scope remain elusive. In this Account, we summarize the progress recorded in this field over the past 15 years. |
| 语种 | 英语 |
| WOS记录号 | WOS:000432418000030 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/42787]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Wang, Mei-Xiang; Zhu, Jieping |
| 作者单位 | 1.Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, Inst Chem Sci & Engn, Lab Synth & Nat Prod, BCH5304, CH-1015 Lausanne, Switzerland 2.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 3.Tsinghua Univ, Dept Chem, Lab Bioorgan Phosphorous Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Qian,Wang, De-Xian,Wang, Mei-Xiang,et al. Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions[J]. ACCOUNTS OF CHEMICAL RESEARCH,2018,51(5):1290-1300. |
| APA | Wang, Qian,Wang, De-Xian,Wang, Mei-Xiang,&Zhu, Jieping.(2018).Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions.ACCOUNTS OF CHEMICAL RESEARCH,51(5),1290-1300. |
| MLA | Wang, Qian,et al."Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions".ACCOUNTS OF CHEMICAL RESEARCH 51.5(2018):1290-1300. |
入库方式： OAI收割
来源：化学研究所
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