Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups | |
Jiang, Quanbin1; Yu, Zhengkun1,2; Guo, Tenglong1 | |
刊名 | JOURNAL OF ORGANIC CHEMISTRY |
2017-02-17 | |
卷号 | 82期号:4页码:1951-1960 |
ISSN号 | 0022-3263 |
DOI | 10.1021/acs.joc.6b02772 |
文献子类 | Article |
英文摘要 | Copper-catalyzed borylation of beta-trifluoromethyl-alpha,beta-unsaturated ketones was efficiently achieved by means of bis(pinacolato)diboron (B(2)pin(2)), affording the enantioenriched pfoducts in good yields with high enantioselectivities. CuI and (R,S)-Josiphos consist of the most efficient catalyst system under mild conditions. In the absence of the chiral ligand, the reactions could be performed more efficiently to form beta-ketone derivatives which were directly borylated and indirectly trifluoromethylated at the beta-carbon atom of the alpha,beta-unsaturated ketone substrates. The present protocol provides a promising method to access a stereogenic carbon center bearing both CF3 and organoboron functional groups. |
WOS关键词 | ELECTRON-DEFICIENT ALKENES ; BORON CONJUGATE ADDITIONS ; ENANTIOSELECTIVE SYNTHESIS ; BETA-BORATION ; ALPHA,BETA-UNSATURATED ACCEPTORS ; BETA,BETA-DISUBSTITUTED ENONES ; ALLYLIC ALCOHOLS ; QUINONE METHIDES ; BOND FORMATION ; ESTERS |
WOS研究方向 | Chemistry |
语种 | 英语 |
出版者 | AMER CHEMICAL SOC |
WOS记录号 | WOS:000394736000011 |
内容类型 | 期刊论文 |
源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169482] |
专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
通讯作者 | Yu, Zhengkun |
作者单位 | 1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China |
推荐引用方式 GB/T 7714 | Jiang, Quanbin,Yu, Zhengkun,Guo, Tenglong. Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(4):1951-1960. |
APA | Jiang, Quanbin,Yu, Zhengkun,&Guo, Tenglong.(2017).Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups.JOURNAL OF ORGANIC CHEMISTRY,82(4),1951-1960. |
MLA | Jiang, Quanbin,et al."Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups".JOURNAL OF ORGANIC CHEMISTRY 82.4(2017):1951-1960. |
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