Title of article
Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); a new ‘metal free’ life for the Rupe rearrangement
Author/Authors
Nandi، نويسنده , , Ganesh C. and Rathman، نويسنده , , Benjamin M. and Laali، نويسنده , , Kenneth K.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2013
Pages
6
From page
6258
To page
6263
Abstract
A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Brønsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.
Keywords
Conjugated enones , Propargylic alcohols , Metal free Rupe rearrangement , Imidazolium ionic liquids , recycling/reuse , Rupe–Aldol–Nazarov sequence
Journal title
Tetrahedron Letters
Serial Year
2013
Journal title
Tetrahedron Letters
Record number
1886595
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