Reactions of <i>N</i>-Arylsulfonyl-2,3-<i>cis</i>- and <i>N</i>-Arylsulfonyl-2,3-<i>trans</i>-3-alkyl-2-vinylaziridines with Organocopper Reagents: Importance of 2,3-<i>cis</i>-Stereochemistry in Controlling Regio- and Stereoselectivity

Abstract

Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic (E)-allylamines. It is also found that the reaction proceeds via the well-known anti-S(N)2' pathway.