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, Wen-Wei Lin

Research output: Contribution to journalArticle

12 Citations (Scopus)

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

Fingerprint

Coumarins
Cycloaddition
Cycloaddition Reaction
Cinchona Alkaloids
Derivatives
pyrrolidine
azomethine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives. / Chang, Geng Hua; Wang, Chein Yi; Madhusudhan Reddy, G.; Tsai, Yi Ling; Lin, Wen-Wei.

In: Journal of Organic Chemistry, Vol. 81, No. 20, 21.10.2016, p. 10071-10080.

Research output: Contribution to journalArticle

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