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DOI | 10.1126/science.aat4210 |
Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction | |
Chen, Jianfeng1,2,3; Gong, Xing1,2; Li, Jianyu1,2; Li, Yingkun1,2; Ma, Jiguo1,2; Hou, Chengkang1,2; Zhao, Guoqing1,2; Yuan, Weicheng3; Zhao, Baoguo1,2 | |
2018-06-29 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 360期号:6396页码:1438-+ |
文章类型 | Article |
语种 | 英语 |
国家 | Peoples R China |
英文摘要 | Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for alpha-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000436598000071 |
WOS关键词 | ALPHA-AMINO-ACIDS ; CLAISEN-TYPE ADDITION ; L-THREONINE ALDOLASE ; ENANTIOSELECTIVE SYNTHESIS ; ENZYMATIC-SYNTHESIS ; ESCHERICHIA-COLI ; PYRIDOXAL ; ORGANOCATALYSIS ; TRANSAMINATION ; GLYCINE |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/198991 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China; 2.Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China; 3.Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Sichuan, Peoples R China |
推荐引用方式 GB/T 7714 | Chen, Jianfeng,Gong, Xing,Li, Jianyu,et al. Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction[J]. SCIENCE,2018,360(6396):1438-+. |
APA | Chen, Jianfeng.,Gong, Xing.,Li, Jianyu.,Li, Yingkun.,Ma, Jiguo.,...&Zhao, Baoguo.(2018).Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction.SCIENCE,360(6396),1438-+. |
MLA | Chen, Jianfeng,et al."Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction".SCIENCE 360.6396(2018):1438-+. |
条目包含的文件 | 条目无相关文件。 |
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