BiCl_3-mediated opening of epoxides,a facile route to chlorohydrins or amino alcohols:one reagent,two paths

摘要

Opening of epoxides can be an effective means by which a variety of functional groups can be incorporated.In this letter,we outline how variation of conditions,in particular,that of solvent and concentration,give rise to different products using the Lewis acid catalyst BiCl_3.Medicinal chemistry relies on robust,reliable reactions,facilitating the rapid development of new chemical entities(NCEs)available for bio-evaluation.In this arena,it is imperative that NCEs are generated rapidly,often at the expense of synthetic elegance,perhaps more so with the increasing levels of automation available to the medicinal chemist.Accordingly,we are constantly searching for,and developing,such reactions for medicinal applications.Recently,as part of an on-going series of medicinal chemistry programs in our laboratory,we developed a pharmacophore model that demanded the synthesis of small targeted libraries of beta-amino alcohols.