Citation: Fang Lei, Lin Weibin, Chen Chuanfeng. Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates[J]. Chinese Chemical Letters, ;2018, 29(8): 1223-1225. doi: 10.1016/j.cclet.2018.06.007 shu

Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates

Fang Lei ^a,b ,
Lin Weibin ^a,b ,
Chen Chuanfeng ^a,b,,

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Chen Chuanfeng, cchen@iccas.ac.cn
Received Date: 16 March 2018
Revised Date: 28 May 2018
Accepted Date: 31 May 2018
Available Online: 5 August 2018

Figures(1)

Tetrahydrobenzo[5]helicenediol (THB-[5]HDIOL) derivatives as additives for the efficient prolinecatalyzed asymmetric List-Lerner-Barbas (LLB) aldol reactions of bulky aldehyde substrates was described. It was found that with dibromo-substituted helical diols P-4a/M-4a as additives, the prolinecatalyzed LLB aldol reaction of 9-anthraldehyde and acetone gave the product in 83% yield and 99% ee. Transition state models revealed an edge-to-face π-π stacking between the anthracenyl group in TS(R) and the phenyl group of the additive, which might result in the high enantioselectivity.
- Helicenediol,
- Asymmetric aldol reaction,
- Additive,
- Bulky aldehyde substrate
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