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

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

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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.

Original languageEnglish
Pages (from-to)10071-10080
Number of pages10
JournalJournal of Organic Chemistry
Volume81
Issue number20
DOIs
Publication statusPublished - 2016 Oct 21

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ASJC Scopus subject areas

  • Organic Chemistry

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