Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes

Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon–carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene....

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Veröffentlicht in:Journal of the American Chemical Society 2013-03, Vol.135 (11), p.4167-4170
Hauptverfasser: McCammant, Matthew S, Liao, Longyan, Sigman, Matthew S
Format: Artikel
Sprache:eng
Schlagworte:
Butadienes - chemical synthesis
Butadienes - chemistry
Catalysis
DNA-Directed RNA Polymerases - antagonists & inhibitors
Lactones - chemical synthesis
Lactones - chemistry
Palladium - chemistry
Polyenes - chemical synthesis
Polyenes - chemistry
Stereoisomerism
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Zusammenfassung:A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon–carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3110544