ol902550q_si_001.pdf (131.78 kB)

Unprotected Vinyl Aziridines: Facile Synthesis and Cascade Transformations

Download (131.78 kB)
journal contribution
posted on 15.01.2010 by Sivaraj Baktharaman, Nicholas Afagh, Adelle Vandersteen, Andrei K. Yudin
Functionalized vinylaziridines, readily available from water-stable aziridine aldehydes have led to the construction of a variety of stereochemically rich heterobicycles. A cascade ring-opening/ring-contraction mechanism operates in the course of the process. These results underscore the notion that interesting and useful nitrogen-mediated relay processes can arise when elements of strain are merged with the manifolds of enamine/iminium ion reactivity.