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Synfacts 2009(9): 1010-1010
DOI: 10.1055/s-0029-1217642
DOI: 10.1055/s-0029-1217642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Cyclobutanones via Ring Expansion of Allenylcyclopropanols
F. Kleinbeck, F. D. Toste*
University of California, Berkeley, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. August 2009 (online)
Significance
The gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols is described. This protocol provides cyclobutanones with a vinyl-substituted quaternary stereogenic center in good yield and with high enantioselectivity. The proposed mechanism for the reaction involves ring expansion by a Wagner-Meerwein shift and is reported to be the first account of an enantioselective gold-catalyzed 1,2-alkyl migration.