Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

doi:10.1007/s40242-014-4061-7

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (4): 596-600.doi: 10.1007/s40242-014-4061-7

Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

CAO Long¹, ZHOU Xiaohong¹, CHEN Jie¹, ZHANG Hui³, DENG Hongmei³, SHAO Min³, McMILLS Mark C.⁴, CAO Weiguo^1,2

1. Department of Chemistry, Shanghai University, Shanghai 200444, P. R. China;
2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China;
3. Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. China;
4. Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA

出版日期:2014-08-01 发布日期:2014-05-12
通讯作者: McMILLS Mark C, CAO Weiguo E-mail:wgcao@staff.shu.edu.cn;mcmills@ohio.edu
基金资助:
Supported by the National Natural Science Foundation of China(No.21272152).

Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

CAO Long¹, ZHOU Xiaohong¹, CHEN Jie¹, ZHANG Hui³, DENG Hongmei³, SHAO Min³, McMILLS Mark C.⁴, CAO Weiguo^1,2

1. Department of Chemistry, Shanghai University, Shanghai 200444, P. R. China;
2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China;
3. Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. China;
4. Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA

Online:2014-08-01 Published:2014-05-12
Contact: McMILLS Mark C, CAO Weiguo E-mail:wgcao@staff.shu.edu.cn;mcmills@ohio.edu
Supported by:
Supported by the National Natural Science Foundation of China(No.21272152).

摘要/Abstract

摘要：

Trans-2,3-dihydrofuran derivatives 3 or 4 substituted with a sulfonyl group were prepared with high chemoselectivity and good yields by [1+4]-addition reaction of α,β-unsaturated ketones 1 with arsonium bromide 2 in CH₂Cl₂ in the presence of potassium carbonate at room temperature. The structures of the products were characterized by IR, MS, ¹H NMR, elemental analysis and single crystal X-ray diffraction analysis. A mechanism for the formation of products was also proposed.

关键词: Stereoselectivity, Dihydrofuran, Arsonium Ylide

Abstract:

Key words: Stereoselectivity, Dihydrofuran, Arsonium Ylide

CAO Long, ZHOU Xiaohong, CHEN Jie, ZHANG Hui, DENG Hongmei, SHAO Min, McMILLS Mark C., CAO Weiguo. Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones[J]. 高等学校化学研究, 2014, 30(4): 596-600.

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Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

Stereoselective Synthesis of Sulfonyl-substituted trans-2,3-Dihydrofuran Derivatives via Reaction of Arsonium Ylides with α,β-Unsaturated Ketones

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