Enantioselective Synthesis of Highly Substituted Chromans by a Zinc(II)-Catalyzed Tandem Friedel–Crafts Alkylation/Michael Addition Reaction

Chao Li; Feng-Lei Liu; You-Quan Zou; Liang-Qiu Lu; Jia-Rong Chen; Wen-Jing Xiao

doi:10.1055/s-0032-1318200

Synthesis, Table of Contents

Synthesis 2013; 45(5): 601-608
DOI: 10.1055/s-0032-1318200

paper

Enantioselective Synthesis of Highly Substituted Chromans by a Zinc(II)-Catalyzed Tandem Friedel–Crafts Alkylation/Michael Addition Reaction

Chao 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: wxiao@mail.ccnu.edu

,

Feng-Lei 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: wxiao@mail.ccnu.edu

,

You-Quan Zou

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: wxiao@mail.ccnu.edu

,

Liang-Qiu Lu

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: wxiao@mail.ccnu.edu

,

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: wxiao@mail.ccnu.edu

,

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: wxiao@mail.ccnu.edu

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Abstract

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Abstract

An enantioselective tandem Friedel–Crafts alkylation/ Michael addition reaction of 1-methylindoles with nitroolefin enoates catalyzed by a chiral tridentate bisoxazoline-Zn(II) complex has been described. This method provides an efficient route to highly substituted chromans in good isolated yields with high stereoselectivities (up to 95:5 dr and 91% ee).

Key words

tandem reaction - Friedel–Crafts alkylation - 1-methylindole - chroman - nitroolefin enoate

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References

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