Cobalt?Catalyzed Hydroalkynylation of Vinylaziridines

Iridium-catalyzed asymmetric hydroalkynylation reactions of oxabenzonorbornadienes.

Oxabenzonorbornadienes were found to be suitable substrates for asymmetric hydroalkynylation reactions. Catalyzed by the complex of [Ir(COD)Cl](2) and (R)-SYNPHOS, oxabenzonorbornadienes and terminal alkynes could react smoothly to give the alkynylated products in moderate to good yields (up to 93% yield) and enantioselectivities (up to 85% ee).

Synthesis and applications of vinylaziridines and ethynylaziridines.

Ring expansion of vinylaziridines through the strain-release pericyclic reaction: recent developments and applications.

Recent syntheses of azetidines, pyrrolidines, piperidines and azepines through cycloaddition or sigmatropic rearrangements of vinylaziridines are described. Applications to natural product synthesis and mechanistic investigations are also summarized.

A Facile Reaction of Unactivated Imines with Telluronium Allylide. Highly Stereoselective Synthesis of Vinylaziridines

Supporting Information General methods. Infrared spectra were recorded on a Nicolet AVATAR-360 spectrometer. H NMR and C NMR spectra were recorded at Bruker AM-300 instruments. Low resolution mass spectra (m/z) were recorded on HP5989A. High-resolution mass spectra were recorded on Concept 1H or MALDI/DHB. Microanalyses were performed using a Elemantar Vario EL. All reaction flasks were dried b...

Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines.

The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2' mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum ...