Gold(I)-Catalyzed Conia-Ene Reaction of β-Ketoesters with Alkynes

Journal of the American Chemical Society

Volumn 126, Issue 14, 2004, Pages 4526-4527

  Kennedy Smith, Joshua J ^a   Staben, Steven T ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BETA KETO ESTER; CARBON; ESTER DERIVATIVE; GOLD; KETONE; PHOSPHINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 1842637760     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049487s     Document Type: Article

References (35)

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33. In accord with this hypothesis diester 37 and ketoamide 38 (enol form destabilized by 1,3-allylic strain) fail to participate in the reaction.
34. This mechanism also provides an explanation for the poor reactivity (<10% conversion) of non-terminal alkynes, since severe 1,3-allylic strain develops in the transition state (A) for cyclization.
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