Asymmetric Boration of Chalcones Catalyzed by Bifunctional[2.2]Paracyclophane-Based N-Heterocyclic Carbene

doi:10.6023/cjoc201706035

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2919-2928.DOI: 10.6023/cjoc201706035 Previous Articles Next Articles

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双功能[2.2]对环蕃基氮杂环卡宾催化查尔酮的不对称硼化反应的研究

叶梦^a, 申盼盼^a, 段文增^b, 宋淳^a, 马玉道^a

a 山东大学化学与化工学院济南 250100;
b 聊城大学化学与化工学院聊城 252000

收稿日期:2017-06-27 修回日期:2017-08-12 发布日期:2017-08-16
通讯作者: 宋淳, 马玉道 E-mail:ydma@sdu.edu.cn;chunsong@sdu.edu.cn
基金资助:
国家自然科学基金（Nos.21372144，81473085）资助项目.

Asymmetric Boration of Chalcones Catalyzed by Bifunctional[2.2]Paracyclophane-Based N-Heterocyclic Carbene

Ye Meng^a, Shen Panpan^a, Duan Wenzeng^b, Song Chun^a, Ma Yudao^a

a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100;
b School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000

Received:2017-06-27 Revised:2017-08-12 Published:2017-08-16
Contact: 10.6023/cjoc201706035 E-mail:ydma@sdu.edu.cn;chunsong@sdu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372144, 81473085).

1. Asymmetric Boration of Chalcones Catalyzed by Bifunctional[2.2]Paracyclophane-Based N-Heterocyclic Carbene.PDF(2214KB)

Abstract

A robust chiral N-heterocyclic carbene precursor based on[2.2]paracyclophane was designed and synthesized for a highly enantioselective metal-free catalytic boration. Enantioselective 1,4-addition of a commercially available bis(pinacolato)-diboron (B₂(pin)₂) to chalcones was achieved by using the new bifunctional chiral carbene as catalyst, affording the corresponding products in up to 99% yield and 97% enantiomeric excess. Moreover, it was found that water used as the additive plays a key role in the carbene-catalyzed enantioselective boration.

Key words: organocatalysis, asymmetric catalysis, carbenes, boron compounds, [2.2]paracyclophane

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Ye Meng, Shen Panpan, Duan Wenzeng, Song Chun, Ma Yudao. Asymmetric Boration of Chalcones Catalyzed by Bifunctional[2.2]Paracyclophane-Based N-Heterocyclic Carbene[J]. Chin. J. Org. Chem., 2017, 37(11): 2919-2928.

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双功能[2.2]对环蕃基氮杂环卡宾催化查尔酮的不对称硼化反应的研究

Asymmetric Boration of Chalcones Catalyzed by Bifunctional[2.2]Paracyclophane-Based N-Heterocyclic Carbene

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