Chiral chromenes are found in a large variety of natural products which are well-known for their useful biological properties. Keeping this in mind, an enantioselective method has been developed for the synthesis of pyran[4,3-b]chromene derivatives,via organocatalyzed [3+2] cycloaddition. Cinchona alkaloid derived organocatalysts have been utilized as chiral bases for the asymmetric [3+2] cycloaddition of o-hydroxy aromatic aldimines and coumarins. Following a very simple protocol which tolerates both moisture and air, a broad range of products were obtained in good to excellent yields and with excellent enantiomeric induction. Moreover, although two stererogenic centers are formed, the products were obtained as single diastereomers.

Enantioselective synthesis of polysubstituted benzopyrano[3,4-<i>c</i>] pyrrolidine for C-C/C-N bond formation via Cinchona alkaloid scaffold

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Enantioselective synthesis of polysubstituted benzopyrano[3,4-c] pyrrolidine for C-C/C-N bond formation via Cinchona alkaloid scaffold