Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives
Autor: | Chein Yi Wang, Wenwei Lin, Geng Hua Chang, Yi Ling Tsai, G. Madhusudhan Reddy |
---|---|
Rok vydání: | 2016 |
Předmět: |
chemistry.chemical_classification
Aldimine biology 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Cinchona 010402 general chemistry biology.organism_classification Coumarin 01 natural sciences Cycloaddition Pyrrolidine 0104 chemical sciences chemistry.chemical_compound Moiety heterocyclic compounds Brønsted–Lowry acid–base theory |
Zdroj: | The Journal of Organic Chemistry. 81:10071-10080 |
ISSN: | 1520-6904 0022-3263 |
DOI: | 10.1021/acs.joc.6b02041 |
Popis: | 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. |
Databáze: | OpenAIRE |
Externí odkaz: |