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Synfacts 2010(3): 0325-0325
DOI: 10.1055/s-0029-1219324
DOI: 10.1055/s-0029-1219324
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific Synthesis of Tetrasubstituted Alkenes via Sc-Catalyzed Methylalumination
M. Takimoto, S. Usami, Z. Hou*
RIKEN Advanced Science Institute, Saitama, Japan
Further Information
Publication History
Publication Date:
18 February 2010 (online)
Significance
The paper described a regio- and stereospecific methylalumination of silyloxy and alkoxy alkynes and alkenes catalyzed by scandium complexes. The stereochemistry of the alkyne addition products is controlled by the substituent on the triple bond. Phenyl and alkyl groups facilitate a syn addition with methyl at the distal position of the ether moiety; the trimethylsilyl group facilitates an anti addition with methyl at the proximal position of the ether moiety.