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Chang GH, Wang CY, Madhusudhan Reddy G, et al. Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives. J Org Chem. 2016;81(20):10071-10080doi: 10.1021/acs.joc.6b02041.
Chang, G. H., Wang, C. Y., Madhusudhan Reddy, G., Tsai, Y. L., & Lin, W. (2016). Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives. The Journal of organic chemistry, 81(20), 10071-10080. https://doi.org/10.1021/acs.joc.6b02041
Chang, Geng-Hua, et al. "Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives." The Journal of organic chemistry vol. 81,20 (2016): 10071-10080. doi: https://doi.org/10.1021/acs.joc.6b02041
Chang GH, Wang CY, Madhusudhan Reddy G, Tsai YL, Lin W. Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives. J Org Chem. 2016 Oct 21;81(20):10071-10080. doi: 10.1021/acs.joc.6b02041. Epub 2016 Oct 04. PMID: 27668513.
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J Org Chem. 2016 Oct 21;81(20):10071-10080. doi: 10.1021/acs.joc.6b02041. Epub 2016 Oct 04.

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives.

The Journal of organic chemistry

Geng-Hua Chang, Chein-Yi Wang, G Madhusudhan Reddy, Yi-Ling Tsai, Wenwei Lin

Affiliations

  1. Department of Chemistry, National Taiwan Normal University , Taipei 11677, Taiwan, R.O.C.

PMID: 27668513 DOI: 10.1021/acs.joc.6b02041

Abstract

An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

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