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Synfacts 2008(9): 0952-0953
DOI: 10.1055/s-2008-1078637
DOI: 10.1055/s-2008-1078637
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Nickel-Catalyzed Stereoselective Synthesis of Z-Enol Silanes
A. Herath, J. Montgomery*
University of Michigan, Ann Arbor, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. August 2008 (online)
Significance
A novel three-component coupling of enals, alkynes, and silanes is achieved under nickel-catalyzed conditions. The reaction is highly selective for the Z-isomer and highly functional-group tolerant, giving a broad scope for each component. In some cases, in situ formation of the aldehyde occurs due to the instability of the corresponding silyl enol ethers. However, most products are functionalized silanes that can be used for further transformations such as Mukaiyama aldol reactions.