Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond To Form Two Stereogenic Centers in an Aqueous Medium

被引：27

作者：

Chen, Zhili ^{[1
]}

Hu, Fangli ^{[1
]}

Huang, Shengli ^{[1
,2
]}

Zhao, Zhengxing ^{[1
]}

Mao, Hui ^{[3
]}

Qin, Wenling ^{[1
]}

机构：

[1] Chongqing Univ, Chongqing Key Lab Nat Prod Synth & Drug Res, Sch Pharmaceut Sci, Chongqing 401331, Peoples R China

[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 401331, Peoples R China

[3] Jinhua Polytech, Pharmaceut & Mat Engn Sch, Jinhua 321000, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 12期

关键词：

ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; WATER; ORGANOSELENIUM; DISELENIDES; SULFONES; KETONES; ACID;

D O I：

10.1021/acs.joc.9b00973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalytic selenosulfonylation of the C-C double bond of alpha,beta-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of alpha-selenyl and beta-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.

引用

页码：8100 / 8111

页数：12

共 43 条

[41] Novel cyclohexene derivatives as anti-sepsis agents: Synthetic studies and inhibition of NO and cytokine production [J].

Yamada, Masami ;

Ichikawa, Takashi ;

Ii, Masayuki ;

Itoh, Katsumi ;

Tamura, Norikazu ;

Kitazaki, Tomoyuki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) :3941-3958

[42] Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation [J].

Yan, Qiaozhi ;

Xiao, Guiying ;

Wang, Ying ;

Zi, Guofu ;

Zhang, Zhanbin ;

Hou, Guohua .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (04) :1749-1756

[43] Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds [J].

Zhou, Taigang ;

Peters, Byron ;

Maldonado, Matias F. ;

Govender, Thavendran ;

Andersson, Pher G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13592-13595

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