61892-18-0Relevant academic research and scientific papers
Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction
Davies, Huw M. L.,Dai, Xing
, p. 6680 - 6684 (2005)
A highly stereoselective formal inverse electron demand hetero Diels-Alder reaction (HDA) occurs on reaction of 2-aryl-α,β-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement.
Silanes in Organic Synthesis. 8. Preparation of Vinylsilanes from Ketones and Their Regiospecific Cyclopentenone Annulation
Paquette, Leo A.,Fristad, William E.,Dime, David S.,Bailey, Thomas R.
, p. 3017 - 3028 (2007/10/02)
A general method is described for the formation of vinylsilanes from ketones.Thus, conversion to the benzene- or p-toluenesulfonylhydrazone and sequential treatment with n-butyllithium and chlorotrimethylsilane in anhydrous tetramethylethylenediamine proceeds regiospecifically to afford the less substituted vinylsilane (in unsymmetrical cases).Friedel-Crafts acylation with acryloyl chlorides and aluminium chloride and subsequent Nazarov cyclization with Lewis acid catalysis results in cyclopentenone annulation.Numerous examples that reveal the scope of this processare described.Due to accompanying polymerization, annulation with acryloyl chloride itself is least efficient.This complication can, however, be averted through use of β-chloropropionyl chloride and dehydrochlorination with 1,5-diazabicycloundec-5-ene prior to ring closure.
