Chiral Squaramide Catalyzed Asymmetric Conjugate Additions of 3-Substituted Oxindoles to Vinylphosphonates

Shu-Wen Duan; Yi-Yin Liu; Wei Ding; Tian-Ren Li; De-Qing Shi; Jia-Rong Chen; Wen-Jing Xiao

doi:10.1055/s-0032-1316919

Synthesis, Table of Contents

Synthesis 2013; 45(12): 1647-1653
DOI: 10.1055/s-0032-1316919

special topic

Chiral Squaramide Catalyzed Asymmetric Conjugate Additions of 3-Substituted Oxindoles to Vinylphosphonates

Shu-Wen Duan

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

Yi-Yin Liu

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

Wei Ding

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

Tian-Ren Li

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

De-Qing Shi

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

Jia-Rong Chen*

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

,

Wen-Jing Xiao*

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China Fax: +86(27)67862041 Email: jiarongchen2003@yahoo.com.cn Email: wxiao@mail.ccnu.edu.cn

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Abstract

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Abstract

An efficient organocatalytic enantioselective conjugate addition of 3-substituted oxindoles to activated vinylphosphonates has been described. This reaction allows the facile synthesis of a new family of organophosphorus derivatives bearing an oxindole motif in high chemical yields with good to excellent stereoselectivities.

Key words

organophosphorus compounds - conjugate addition - oxindole - organocatalysis - squaramide catalyst

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References

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14 Please see Supporting Information for X-ray crystal structure for compound 4 (CCDC 921101).

Supplementary Material

Supporting Information