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Synthesis 1995; 1995(8): 1003-1006
DOI: 10.1055/s-1995-4034
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Efficient Synthesis of Branched Propargyl- and Allylsilanes

Lutz F. Tietze* , Thomas Neumann, Masahiro Kajino, Martina Pretor
  • *Institute of Organic Chemistry of the Georg-August-University, Tammannstrasse 2, D-37077 Göttingen (FAX number: 49/(0)551/399476)
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Publication Date:
31 December 2000 (online)

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The transformation of α-silylated aldehydes 3a-h into the propargylsilanes 5a-k and the (Z)-allylsilane 6 is described. The readily available tert-butylimine 1 of acetaldehyde is silylated and alkylated in a one-pot procedure to obtain the α-silylated aldehydes 3a-h after hydrolysis of the imine moiety in 77-96% yield. C-1 homologation by the Corey-Fuchs method gave 1,1-dibromoallylsilanes 4a-h in 70-96% yields which can be transformed into the mono- and disubstituted propargylsilanes 5a-k in 33-95% yield. Hydrogenation of the propargylsilanes e.g. 5e with Ni(OAc)2/NaBH4 gives the (Z)-allylsilane 6a in 80% yield.

α-silylaldehydes - 1,1-dibromoallylsilanes - propargylsilanes - (Z)-allylsilane - Corey-Fuchs transformation