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

共 88 条

[21] Baker's yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal [J].

Fuganti, C ;

Serra, S ;

Dulio, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :279-282

[22] A Heterobimetallic Ni/La-salan Complex for Catalytic Asymmetric Decarboxylative 1,4-Addition of Malonic Acid Half-Thioester [J].

Furutachi, Makoto ;

Mouri, Shinsuke ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (11) :2351-2354

[23] Catalysis for fluorination and trifluoromethylation [J].

Furuya, Takeru ;

Kamlet, Adam S. ;

Ritter, Tobias .

NATURE, 2011, 473 (7348) :470-477

[24] Chiral NG-acylated hetarylpropylguanidine-type histamine H2 receptor agonists do not show significant stereoselectivity [J].

Ghorai, Prasanta ;

Kraus, Anja ;

Birnkammer, Tobias ;

Geyer, Roland ;

Bernhardt, Guenther ;

Dove, Stefan ;

Seifert, Roland ;

Elz, Sigurd ;

Buschauer, Armin .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (10) :3173-3176

[25]

Gremaud L., 2012, ANGEW CHEM, V124, P818

[26] Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoesters [J].

Gremaud, Ludovic ;

Alexakis, Alexandre .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) :794-797

[27] Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts [J].

Hara, Noriyuki ;

Nakamura, Shuichi ;

Sano, Masahide ;

Tamura, Ryota ;

Funahashi, Yasuhiro ;

Shibata, Norio .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9276-9280

[28] Organocatalytic Enantioselective Decarboxylative Addition of Malonic Acids Half Thioesters to Isatins [J].

Hara, Noriyuki ;

Nakamura, Shuichi ;

Funahashi, Yasuhiro ;

Shibata, Norio .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :2976-2980

[29] The biosynthesis, molecular genetics and enzymology of the polyketide-derived metabolites [J].

Hill, AM .

NATURAL PRODUCT REPORTS, 2006, 23 (02) :256-320

[30]

Hiyama T., 2013, ORGANOFLUORINE COMPO

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