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:
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