Asymmetric Decarboxylative 1, 4??Addition of Malonic Acid Half Thioesters to Vinyl Sulfones: Highly Enantioselective Synthesis of 3??Monofluoromethyl??3?? …

B Qiao, Q Liu, H Liu, L Yan…

Index: Qiao, Baokun; Liu, Qian; Liu, Hongjun; Yan, Lin; Jiang, Zhiyong Chemistry - An Asian Journal, 2014 , vol. 9, # 5 p. 1252 - 1256

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Citation Number: 6

Abstract

Abstract 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 ...