A convenient conversion of terminal alkenes into homologous unsaturated and doubly unsaturated esters

Bill Hawkins (1) , Victoria L. Paddock (1) , Nina Tölle (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives α,β-unsaturated esters, which coupled with a xanthate elimination yields α,β,γ,δ-unsaturated esters. © 2012 American Chemical Society.

Domains: Chemical Sciences; Organic chemistry

Bill Hawkins, Victoria L. Paddock, Nina Tölle, Samir Z. Zard. A convenient conversion of terminal alkenes into homologous unsaturated and doubly unsaturated esters. Organic Letters, 2012, 14 (4), pp.1020-1023. ⟨10.1021/ol203387r⟩. ⟨hal-00949979⟩