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Synthesis 1997; 1997(2): 150-152
DOI: 10.1055/s-1997-1160
short paper
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A One-Pot Preparation of Allylsilanes and (Z)-Alk-2-enylsilanes

Olivier Desponds, Livia Franzini, Manfred Schlosser*
  • *Institut de Chimie organique de l’Université, Bâtiment de Chimie (BCh), CH-1015 Lausanne-Dorigny, Switzerland, Fax +41(21)6923965
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Publication Date:
31 December 2000 (online)

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Metalation of alk-1-enes, using the mixture of butyllithium and potassium tert-butoxide in tetrahydropyran, followed by stereohomogenization and ultimate treatment with chlorotrimethylsilane afforded a series of alk-2-enyltrimethylsilanes in good yield and with (Z/E) ratios ranging from 95:5 to 98:2. The deprotonation of propene can be rapidly and readily accomplished with a stoichiometric amount of the superbase suspended in pentane on a 1 mol scale.

allylpotassium - metalation of terminal olefins - superbases - allyl type silanes - stereoselectivity