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Synfacts 2011(6): 0627-0627
DOI: 10.1055/s-0030-1260431
DOI: 10.1055/s-0030-1260431
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Ruthenium-Catalyzed Asymmetric [2+2] Cycloaddition of Ynamides with Enones
Contributor(s):Hisashi Yamamoto, Patrick BradyC. Schotes, A. Mezzetti*
ETH Zürich, Switzerland
Enantioselective Ficini Reaction: Ruthenium/PNNP-Catalyzed [2+2] Cycloaddition of Ynamides with Cyclic Enones
Angew. Chem. Int. Ed. 2011, 50: 3072-3074
ETH Zürich, Switzerland
Enantioselective Ficini Reaction: Ruthenium/PNNP-Catalyzed [2+2] Cycloaddition of Ynamides with Cyclic Enones
Angew. Chem. Int. Ed. 2011, 50: 3072-3074
Further Information
Publication History
Publication Date:
19 May 2011 (online)
Key words
[2+2] cycloaddition - enones - ruthenium
Significance
The chiral dicationic ruthenium complex catalyzes the asymmetric [2+2] cycloaddition of cyclic β-keto esters with ynamides. The reaction tolerates a wide range of substrates and generates an all-carbon quaternary stereogenic center in high yield and with high asymmetric induction.
Comment
Ynamides bearing an electron-deficient and an electron-donating group were found to be ideal substrates for this reaction due to the absence of an uncatalyzed background reaction at elevated temperatures.