A Bench-Stable Vilsmeier Reagent for in situ Alcohol Activation: Synthetic Application in the Synthesis of 2-Amino-2-Thiazolines
Received: 15 June 2017
Accepted: 04 July 2017
16 August 2017 (eFirst)
This paper is dedicated to Professor Vic Snieckus in honor of his 80th birthday
A robust, chemoselective direct condensation/cyclization of thioureas and amino alcohols is described. Employing a bench-stable Vilsmeier reagent, methoxymethylene-N,N-dimethyliminium methyl sulfate, the selective in situ activation of alcohols is achieved with high efficiency and broad functional-group tolerance. The reversible interaction of the Vilsmeier reagent with substrate was key to the success of this activation strategy.