Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Jhen Kuei Yu; Han Wei Chien; Yi Jung Lin; Praneeth Karanam; Yu Heng Chen; Wenwei Lin

doi:10.1039/c8cc05693e

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Jhen Kuei Yu, Han Wei Chien, Yi Jung Lin, Praneeth Karanam, Yu Heng Chen, Wenwei Lin

Department of Chemistry

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.

Original language	English
Pages (from-to)	9921-9924
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	71
DOIs	https://doi.org/10.1039/c8cc05693e
Publication status	Published - 2018 Jan 1

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Cycloaddition

Cycloaddition Reaction

azomethine

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Cite this

Yu, J. K., Chien, H. W., Lin, Y. J., Karanam, P., Chen, Y. H., & Lin, W. (2018). Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition. Chemical Communications, 54(71), 9921-9924. https://doi.org/10.1039/c8cc05693e

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition. / Yu, Jhen Kuei; Chien, Han Wei; Lin, Yi Jung; Karanam, Praneeth; Chen, Yu Heng; Lin, Wenwei.

In: Chemical Communications, Vol. 54, No. 71, 01.01.2018, p. 9921-9924.

Research output: Contribution to journal › Article

Yu, JK, Chien, HW, Lin, YJ, Karanam, P, Chen, YH & Lin, W 2018, 'Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition', Chemical Communications, vol. 54, no. 71, pp. 9921-9924. https://doi.org/10.1039/c8cc05693e

Yu JK, Chien HW, Lin YJ, Karanam P, Chen YH, Lin W. Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition. Chemical Communications. 2018 Jan 1;54(71):9921-9924. https://doi.org/10.1039/c8cc05693e

Yu, Jhen Kuei ; Chien, Han Wei ; Lin, Yi Jung ; Karanam, Praneeth ; Chen, Yu Heng ; Lin, Wenwei. / Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition. In: Chemical Communications. 2018 ; Vol. 54, No. 71. pp. 9921-9924.

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10.1039/c8cc05693e