Citation: Xie Xiaojuan, Zhang Zhong, Zhao Huaxin, Wan Wen, Hao Jian. Trifluoromethylated-Imidazolines as Efficient Organocatalyst for Asymmetric Aldol Reaction of Hydroxyacetone with Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 117-121. doi: 10.6023/cjoc201809026 shu

Trifluoromethylated-Imidazolines as Efficient Organocatalyst for Asymmetric Aldol Reaction of Hydroxyacetone with Aldehydes

Xie Xiaojuan ^a ,
Zhang Zhong ^a ,
Zhao Huaxin ^a ,
Wan Wen ^a,b,, ,
Hao Jian ^a,b,,

a.
Department of Chemistry, Shanghai University, Shanghai 200444
b.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Wan Wen, wanwen@shu.edu.cn Hao Jian, jhao@shu.edu.cn
Received Date: 21 September 2018
Revised Date: 5 December 2018
Available Online: 7 January 2018
Fund Project: the National Natural Science Foundation of China 21572128the National Natural Science Foundation of China 21672139Project supported by the National Natural Science Foundation of China (Nos. 21572128, 21672139) and the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science

Figures(2)

Aldol reaction of hydroxyacetone is an all-purpose route to construct the 1, 2-diol building blocks for the synthesis of multifarious natural products and biological active molecules. In this work, a new series of trifluoromethylated-imidazoline organocatalysts have been designed and synthesized. It is found that the trifluoromethylated chiral organocatalyst (2R, 4S)-4-benzyl-1, 2-dimethyl-2-(trifluoromethyl) imidazolidine (1a) has proved to be very efficient for the direct asymmetric aldol reaction of α-hydroxyketones with aldehydes to build the syn-1, 2-diol building blocks. Among the synthesized syn-aldol products, a good yield (up to 96%) and high stereoselectivity (up to dr＝15:1, 99% ee) could be obtained. The F—H bonding derived from trifluoromethyl group was proposed to play an important role in the stabilization of the transition state.
- asymmetric aldol reaction,
- organocatalysis,
- imidazoline,
- trifluoromethyl,
- synthesis
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