Catalytic Asymmetric Conjugate Addition of Tritylthiol to Azadienes with a Bifunctional Organocatalyst

被引：45

作者：

Gu, Zheng ^{[1
]}

Xie, Jiao-Jiao ^{[1
]}

Jiang, Guo-Fang ^{[1
]}

Zhou, Yong-Gui ^{[2
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 08期

基金：

中国国家自然科学基金;

关键词：

azadienes; organocatalysis; enantioselectivity; sulfa-Michael addition; thiols; SULFA-MICHAEL ADDITION; 3 CONTIGUOUS STEREOCENTERS; N-HETEROCYCLIC CARBENE; ALKYL THIOLS; NONCOVALENT ORGANOCATALYST; ENANTIOSELECTIVE SYNTHESIS; ALDOL REACTIONS; BOND FORMATION; ALPHA; CONSTRUCTION;

D O I：

10.1002/ajoc.201800299

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective sulfa-Michael addition of tritylthiol to azadienes catalyzed by a bifunctional squaramide organocatalyst is described, giving the chiral aminothioethers bearing benzofuran motif with high yields and up to 94% of enantioselectivity. Notably, the aromatization to form the benzofuran is the driving force.

引用

页码：1561 / 1564

页数：4

共 47 条

[1]

[Anonymous], 2015, ANGEW CHEM

[2]

[Anonymous], 2008, ANGEW CHEM

[3] Organocatalytic Carbon-Sulfur Bond-Forming Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Enders, Dieter .

CHEMICAL REVIEWS, 2014, 114 (18) :8807-8864

[4] Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst [J].

Chen, Jiean ;

Meng, Sixuan ;

Wang, Leming ;

Tang, Hongmei ;

Huang, Yong .

CHEMICAL SCIENCE, 2015, 6 (07) :4184-4189

[5] A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water [J].

Chen, Ping ;

Lu, Sheng-mei ;

Guo, Wengang ;

Liu, Yan ;

Li, Can .

CHEMICAL COMMUNICATIONS, 2016, 52 (01) :96-99

[6] Catalytic Asymmetric Conjugate Addition of Mercaptans to β-Substituted-β-Trifluoromethyl Oxazolidinone Enoates: Access to Chiral Trifluoromethylated Tertiary Thioethers and Thiols [J].

Chen, Wenchao ;

Jing, Zhengzhong ;

Chin, Kek Foo ;

Qiao, Baokun ;

Zhao, Yan ;

Yan, Lin ;

Tan, Choon-Hong ;

Jiang, Zhiyong .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) :1292-1300

[7] Chiral Squaramide-Catalyzed Enantioselective Conjugate Michael Addition of Various Thiols to α,β-Unsaturated N-Acylated Oxazolidin-2-ones [J].

Dai, Le ;

Yang, Hongjun ;

Chen, Fener .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (26) :5071-5076

[8] Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis [J].

Dunbar, Kyle L. ;

Scharf, Daniel H. ;

Litomska, Agnieszka ;

Hertweck, Christian .

CHEMICAL REVIEWS, 2017, 117 (08) :5521-5577

[9] Catalytic kinetic resolution reaction of (±)-5-methylbicyclo[3.3.0]oct-1-ene-3,6-dione [J].

Emori, E ;

Iida, T ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5318-5320

[10] A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].

Emori, E ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044

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