Asymmetric Decarboxylative 1,4-Addition of Malonic Acid Half Thioesters to Vinyl Sulfones: Highly Enantioselective Synthesis of 3-Monofluoromethyl3-Arylpropanoic Esters

作者：Qiao, Baokun; Liu, Qian; Liu, Hongjun; Yan, Lin; Jiang, Zhiyong^*

来源：Chemistry-An Asian Journal, 2014, 9(5): 1252-1256.

DOI：10.1002/asia.201400049

• asymmetric synthesis
• decarboxylative 1
• 4-addition
• monofluoromethylation
• organocatalysis
• vinyl sulfones

An asymmetric decarboxylative 1,4-addition of malonic acid half thioesters (MAHTs) to 2-aryl-substituted vinyl sulfones has been developed, yielding adducts with excellent enantioselectivity (up to 97% ee). In view of tuning pK(a) values, a quinine-based benzyl-substituted thiourea was designed and demonstrated as the most efficient catalyst. The enantioselective synthesis of 3-monofluorinated analogues of 3-methyl indanone and (+)-turmerone has been accomplished from decarboxylative 1,4-addition adducts with satisfactory results.

• 出版日期2014-5
• 单位河南大学