Reactions of N-Arylsulfonyl-2,3-cis- and N-Arylsulfonyl-2,3-trans-3-alkyl-2-vinylaziridines with Organocopper Reagents: Importance of 2,3-cis-Stereochemistry in Controlling Regio- and Stereoselectivity.
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.
Toda
Ayako
A
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606, Japan.
Aoyama
Hiroshi
H
Mimura
Norio
N
Ohno
Hiroaki
H
Fujii
Nobutaka
N
Ibuka
Toshiro
T