Enantio- and diastereoselective synthesis of syn-beta-hydroxyallylsilanes via a chiral (Z)-gamma-silylallylboronate.

James B Aggen, Eliana S Armstrong, Adam A Goldblum, Paola Dozzo, Martin S Linsell, Micah J Gliedt, Darin J Hildebrandt, Lee Ann Feeney, Aya Kubo, Rowena D Matias, Sara Lopez, Marcela Gomez, Kenneth B Wlasichuk, Raymond Diokno, George H Miller, Heinz E Moser

Index: Org. Lett. 9 , 4315, (2007)

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Abstract

syn-beta-Hydroxyallylsilanes of general structure 11 and 28 are prepared in 50-86% yield and 91-95% ee (for aliphatic aldehydes; 50% ee for benzaldehyde) via the BF(3).Et(2)O-promoted gamma-silylallylboration reactions, using reagents 14 and 15.