BiCl 3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: one reagent, two paths

A McCluskey, SK Leitch, J Garner, CE Caden, TA Hill…

Index: McCluskey, Adam; Leitch, Sarah K.; Garner, James; Caden, Christine E.; Hill, Timothy A.; Odell, Luke R.; Stewart, Scott G. Tetrahedron Letters, 2005 , vol. 46, # 47 p. 8229 - 8232

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Citation Number: 40

Abstract

There is a considerable literature precedent for the synthesis of β-amino alcohols, with the conversion of epoxides into the corresponding trans amino alcohols being a noteworthy example. 3, 4 and 5 Ring opening of epoxides is traditionally preferable to the ring opening of aziridines, 6 a function of their higher reactivity and ease of synthesis. An additional concern in our laboratory is waste minimization and the application of green chemistry principles. 7 The pharmaceutical ...