Efficient Entry to Tetrahydropyridines: Addition of Enol Ethers to Allenesulfonamides Involving a Novel 1,3-Sulfonyl Shift

Yoshikazu Horino, Masanari Kimura, Yoshinori Wakamiya, Toshiya Okajima, Yoshinao Tamaru

Angewandte Chemie International Edition · 1999 · 35 citations · 0 references

Concepts

Abstract

Heating at 70–100°C is all that is needed to induce a novel 1,3-sulfonyl shift in the reaction of N-allenesulfonamides with enol ethers [Eq. (a)]. Tetrahydropyridine derivatives are obtained in excellent yields and with high stereoselectivities.