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Synfacts 2010(8): 0899-0899
DOI: 10.1055/s-0030-1257777
DOI: 10.1055/s-0030-1257777
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Regiocontrol in the Nickel-Catalyzed Aldehyde-Alkyne Reductive Coupling
H. A. Malik, G. J. Sormunen, J. Montgomery*
University of Michigan, Ann Arbor, USA
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Significance
The reductive coupling of alkynes with aldehydes is a common method for preparing allylic alcohols. When unsymmetrical alkynes are used two regioisomeric products can be formed. Regiocontrol is possible with a strong steric or electronic bias in the alkyne. The authors have developed catalyst systems which are exceptionally sensitive to steric differences in unsymmetrical alkynes, allowing either regioisomeric trisubstituted alkene to be synthesized.