General, Stereoselective Synthesis of (Z)-β,γ-Unsaturated Nitriles Promoted by Samarium Diiodide

General, Stereoselective Synthesis of (Z)-β,γ-Unsaturated Nitriles Promoted by Samarium Diiodide

A method to obtain (Z)-β,γ-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with SmI2. The starting compounds were readily prepared, and a mechanism is pr...

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Veröffentlicht in:Organic letters 2008-10, Vol.10 (20), p.4549-4552
Hauptverfasser: Concellón, José M, Rodríguez-Solla, Humberto, Simal, Carmen, Santos, David, Paz, Nieves R
Format: Artikel
Sprache:eng
Schlagworte:
Iodides - chemistry
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Samarium - chemistry
Stereoisomerism
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Zusammenfassung:A method to obtain (Z)-β,γ-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with SmI2. The starting compounds were readily prepared, and a mechanism is proposed to explain this stereoselective β-elimination reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801752m