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



叶梦a, 申盼盼a, 段文增b, 宋淳a, 马玉道a   

  1. 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;
  • 基金资助:


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

Ye Menga, Shen Panpana, Duan Wenzengb, Song Chuna, Ma Yudaoa   

  1. 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;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21372144, 81473085).

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