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Synfacts 2009(3): 0296-0296
DOI: 10.1055/s-0028-1087758
DOI: 10.1055/s-0028-1087758
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Chiral Silanols from Desymmetrization of Dialkoxysilanes
K. Igawa, J. Takada, T. Shimono, K. Tomooka*
Kyushu University, Fukuoka and Tokyo Institute of Technology, Japan
Further Information
Publication History
Publication Date:
19 February 2009 (online)
Significance
The authors present a novel route to the synthesis of enantiomerically enriched silanols by the desymmetrization of dialkoxysilanes. The reaction proceeds in excellent yields, though with moderate enantioselectivities. Conversion of the initial products into silanols can be accomplished by a Birch reduction. Reactions performed in hexane give higher enantiopurity than those with ether.