C–O and C–C bond formation in the cyclisation of gem-(dialkoxymethyl)-1,6-dienes catalysed by tin(IV) triflimidate at room temperature

Vece, Vito; Hassen, Khadija Ben Hadj; Antoniotti, Sylvain; Duñach, Elisabet

C–O and C–C bond formation in the cyclisation of gem-(dialkoxymethyl)-1,6-dienes catalysed by tin(IV) triflimidate at room temperature

2012

Vece, Vito | Hassen, Khadija Ben Hadj | Antoniotti, Sylvain | Duñach, Elisabet

We described herein a Sn(NTf₂)₄-catalysed cyclisation of gem-(dialkoxymethyl)-1,6-dienes and derivatives where cyclohexane or tetrahydrofuran rings are formed following either a 6-enexo-endo-trig process or a 5-exo-trig process, respectively, depending on substitution patterns. The latter process features an unusual dealkylative ether cyclisation, triggered by the strong Lewis acid character of the tin(IV) triflimidate catalyst.

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