Organocatalytic enantioselective [2+4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines

An enantioselective [2 + 4]-annulation of gamma-substituted allenoates with N-acyldiazenes has been developed for the first time. In the presence of an l-proline-derived DMAP analogue, the annulation proceeded smoothly to afford a broad range of 1,3,4-oxadiazine derivatives in good to excellent yields with high stereoselectivities.

Automated summary

An enantioselective [2 + 4]-annulation of gamma-substituted allenoates with N-acyldiazenes has been developed for the first time, resulting in a broad range of 1,3,4-oxadiazine derivatives in good to excellent yields with high stereoselectivities using an l-proline-derived DMAP analogue as the catalyst.