Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2919-2928. doi: 10.6023/cjoc201706035 shu

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

Corresponding author: Song Chun, chunsong@sdu.edu.cn Ma Yudao, ydma@sdu.edu.cn

^†

Received Date: 27 June 2017
Revised Date: 12 August 2017
Available Online: 16 November 2017
Fund Project: the National Natural Science Foundation of China 81473085Project supported by the National Natural Science Foundation of China (Nos. 21372144, 81473085)the National Natural Science Foundation of China 21372144

Figures(4)

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.
- organocatalysis,
- asymmetric catalysis,
- carbenes,
- boron compounds,
- [2.2]paracyclophane
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