Science Faculty

Asymmetric Synthesis of 1,2-Diamines bearing Tetrasubstituted Centers from Nonstabilized Azomethine Ylides and N‑Sulfinylketimines under Brønsted Acid Catalysis

Author/s

Izquierdo, C.; Esteban, F.; García Ruano, J. L.; Fraile, A.; Alemán, J.

Año de edición

2016

Referencia completa

Org. Lett. 2016, 18, 92−95. DOI: 10.1021/acs.orglett.5b03251

Resumen

The first asymmetric cycloaddition of nonstabilized azomethine ylide and N-sulfinylimines is presented. In reactions with aryl−alkyl and heteroaryl−alkyl ketimines, excellent diastereoselectivities and good yields are obtained in all cases, regardless of the
electronic character of the substituents at the aromatic rings. Moreover, the cycloadducts obtained can easily be deprotected in acid media, giving access to free 1,2-diamines which are prevalent in many natural and pharmaceutical products.