Regio- and Stereoselective Hydroamination of Alkynes Using an Ammonia Surrogate: Synthesis of N‑Silylenamines as Reactive Synthons
datasetposted on 12.03.2018, 00:00 by Erica K. J. Lui, Jason W. Brandt, Laurel L. Schafer
An anti-Markovnikov selective hydroamination of alkynes with N-silylamines to afford N-silylenamines is reported. The reaction is catalyzed by a bis(amidate)bis(amido)Ti(IV) catalyst and is compatible with a variety of terminal and internal alkynes. Stoichiometric mechanistic studies were also performed. This method easily affords interesting N-silylenamine synthons in good to excellent yields and the easily removable silyl protecting group enables the catalytic synthesis of primary amines.