Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes
文献类型：期刊论文
| 作者 | Li, Jiuyuan; Fu, Niankai; Li, Xin; Luo, Sanzhong; Cheng, Jin-Pei |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2010-07-02 |
| 卷号 | 75期号:13页码:4501-4507 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/jo100976e |
| 英文摘要 | Highly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary-tertiary diamine-Bronsted acid salts are found to promote the cross-aldol reactions of aldehydes with high activity and syn selectivity. Among various vicinal diamines screened, L-phenylalanine derived 2a/TfOH conjugate is identified as the optimal catalyst, showing good catalytic activity (up to 97% yield) and high syn selectivities (syn/anti up to 24: I, 87% cc). The current catalysis works selectively with small aliphatic aldehydes donors such as propionaldehyde and isobutyraldehyde, but not with aliphatic aldehydes bearing larger beta-substitute (> Me). In addition, the use of 2a/TfOH conjugate has also enabled the first syn-selective cross-aldol reactions of glycoaldehyde donors. |
| 语种 | 英语 |
| WOS记录号 | WOS:000279030900018 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/69993]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Luo, Sanzhong |
| 作者单位 | Chinese Acad Sci, BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Jiuyuan,Fu, Niankai,Li, Xin,et al. Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(13):4501-4507. |
| APA | Li, Jiuyuan,Fu, Niankai,Li, Xin,Luo, Sanzhong,&Cheng, Jin-Pei.(2010).Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes.JOURNAL OF ORGANIC CHEMISTRY,75(13),4501-4507. |
| MLA | Li, Jiuyuan,et al."Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes".JOURNAL OF ORGANIC CHEMISTRY 75.13(2010):4501-4507. |
入库方式： OAI收割
来源：化学研究所
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