Copper-catalyzed Silylative Allylation of Ketones and Aldehydes Employing Allenes and Silylboranes

• DOI: 10.1246/cl.141018
• Publication Date: 2014-11-21T23:38:22Z
• Authors: Yosuke Tani; Tatsuya Yamaguchi; Tetsuaki Fujihara; Jun Terao; Yasushi Tsuji
• Keywords: 02 engineering and technology; 0210 nano-technology; 01 natural sciences; 0104 chemical sciences

Abstract The copper-catalyzed silylative allylation of ketones with allenes and silylboranes via an in situ generated β-silylallylcopper intermediate has been developed. Various ketones and allenes were converted to the homoallylic tertiary alcohols bearing internal (E)-vinylsilane moieties regio- and stereoselectively in good to high yields. Aldehydes were also employed as electrophiles in the reaction.