A Convenient Method for the Synthesis of β,γ-Unsaturated Amines from Alkenes via α,β-Unsaturated Diphenylsulfonium Salts

Hiroyuki Yamanaka, Jun‐ichi Matsuo, Asahi Kawana, Teruaki Mukaiyama

Chemistry Letters · 2003 · 30 citations · 21 references

Concepts

Abstract

Abstract 1,1-Disubstituted and trisubstituted alkenes were converted into the corresponding β,γ-unsaturated amines 4 via three steps: the initial formation of α,β-unsaturated diphenylsulfonium triflates 2 from alkenes and diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1), followed by double bond migration of 2 to β,γ-unsaturated sulfonium triflates 3 with primary or secondary amines, and successive nucleophilic substitution of 3 with these amines.

References

21