Stereoselective Peterson Olefinations from Bench‐Stable Reagents and N‐Phenyl Imines. Issue 24 (11th March 2015)

• Record Type: Journal Article
• Authors: Das, Manas; Manvar, Atul; Jacolot, Maïwenn; Blangetti, Marco; Jones, Roderick C.; O'Shea, Donal F.
• Is Part Of: Chemistry. Volume 21:Issue 24(2015)
• Page Start: 8737
• Page End: 8740
• Publication Date: 2015-03-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201500475
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The synthesis of bench‐stable α, α‐bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (<italic>E</italic>/<italic>Z</italic> ∼1:1 to 4:1) though this was significantly improved by employing the corresponding substituted <italic>N</italic>‐benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as <italic>N</italic>, <italic>N</italic>‐bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.</p> </abstract>