Synlett
DOI: 10.1055/s-0036-1589086
letter
© Georg Thieme Verlag Stuttgart · New York

A Bench-Stable Vilsmeier Reagent for in situ Alcohol Activation: Synthetic Application in the Synthesis of 2-Amino-2-Thiazolines

Michael T. Corbett*, Seb Caille
  • Pivotal Drug Substance Process Development, Amgen, One Amgen Center Drive, Thousand Oaks, CA 91320, USA   Email: mcorbe01@amgen.com
Further Information

Publication History

Received: 15 June 2017

Accepted: 04 July 2017

Publication Date:
16 August 2017 (eFirst)

This paper is dedicated to Professor Vic Snieckus in honor of his 80th birthday

Abstract

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.

Supporting Information