Synfacts 2009(3): 0296-0296  
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

Contributor(s): Mark Lautens, Praew Thansandote
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.