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.

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收藏

页码：8100 / 8111

页数：12

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