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

被引：23

作者：

Qiao, Baokun ^{[1
]}

Liu, Qian ^{[2
]}

Liu, Hongjun ^{[2
]}

Yan, Lin ^{[1
]}

Jiang, Zhiyong ^{[1
,2
]}

机构：

[1] Henan Univ, Inst Chem Biol, Kaifeng 475004, Henan, Peoples R China

[2] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 05期

关键词：

asymmetric synthesis; decarboxylative; 1; 4-addition; monofluoromethylation; organocatalysis; vinyl sulfones; ORGANOCATALYTIC CONJUGATE ADDITION; MICHAEL-ADDITION; CATALYZED HYDROGENATION; 3-SUBSTITUTED OXINDOLES; POLYKETIDE SYNTHASES; CARBONYL-COMPOUNDS; OXAZOLINE LIGANDS; FLUORINATION; HYDROACYLATION; NITROOLEFINS;

D O I：

10.1002/asia.201400049

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1252 / 1256

页数：5

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