Citation: Hong-Yu Duan, Juan Ma, Zhe-Zhe Yuan, Ri-Sheng Yao, Wei Tao, Fang Xu, Hua Xiao, Gang Zhao. Phosphine-promoted [3 + 2] cycloaddition between nonsubstituted MBH carbonates and trifluoromethyl ketones[J]. Chinese Chemical Letters, ;2015, 26(6): 646-648. doi: 10.1016/j.cclet.2015.03.019 shu

Phosphine-promoted [3 + 2] cycloaddition between nonsubstituted MBH carbonates and trifluoromethyl ketones

Hong-Yu Duan ^a ,
Juan Ma ^a ,
Zhe-Zhe Yuan ^a ,
Ri-Sheng Yao ^a,, ,
Wei Tao ^a ,
Fang Xu ^a ,
Hua Xiao ^a,b,, ,
Gang Zhao ^b

1.
a School of Medical Engineering, Hefei University of Technology, Hefei 230009, China;
2.
b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Ri-Sheng Yao, Hua Xiao,
Received Date: 14 January 2015
Available Online: 4 March 2015
Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21302034) (No. 21302034)

A phosphine-promoted [3 + 2] cycloaddition from readily accessible MBH (Morita-Baylis-Hillman) carbonate and aryl trifluoromethyl ketone is described. The use of methyl vinyl ketone-derived allylic carbonate rather than common acrylate-derived counterpart renders the reaction pathway exclusive for 5-endo process, which enables the expeditious preparation of a range of trifluoromethylated 2, 3-dihydrofuran in a chemospecific manner.
- Cycloaddition,
- Allylic carbonate,
- Ylides,
- Trifluoromethyl ketones
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