Tandem catalytic carbene addition/bicyclization of enynes. One-step synthesis of fluorinated bicyclic amino esters by ruthenium catalysis

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3741-3743

  Eckert, Matthieu ^a   Monnier, Florian ^a   Shchetnikov, Grigorii T ^b   Titanyuk, Igor D ^b   Osipov, Serguej N ^b   Toupet, Loïc ^c   Dérien, Sylvie ^a   Dixneuf, Pierre H ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24044485075     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051393f     Document Type: Article

References (23)

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20. General procedure: in a Schlenk tube under inert atmosphere, to a solution of the enyne (1 mmol) in degassed diethyl ether (2 mL) was added 1.15-1.2 mmol of the 2.0 M trimethylsilyldiazomethane solution in ether. The mixture was stirred at room temperature, and 5 mol % of the precatalyst Cp*RuCl(COD) was then introduced. Pure ethyldiazoacetate was similarly added to a dioxane solution, and the reaction was performed at 100°C. Reaction completion was monitored using GC or TLC techniques. Diastereoisomers were separated as pure compounds using standard chromatography over silica gel with an ether:pentane eluting mixture. All bicyclic compounds were fully characterized.
21. See Supporting Information.
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