Superbases for organic synthesis
Open Access
- 1 January 1988
- journal article
- Published by Walter de Gruyter GmbH
- Vol. 60 (11) , 1627-1634
- https://doi.org/10.1351/pac198860111627
Abstract
LICKOR mixtures of organolithium reagents and bulky potassium alcoholates allow the smooth metalation and subsequent electrophilic substitution of low acidity hydrocarbons, in particular olefm. The allylpotassium intermediates exhibit peculiar conformational preferences which can be exploited in novel stereoselective carbon-carbon linking reactions. A few syntheses of simple natural products illustrate the method. A tentative explanation is given for the superior performance of LICKOR mixtures when compared with butylpotassium.Keywords
This publication has 4 references indexed in Scilit:
- Enantiomeric Z- and E-crotyldiisopinocampheylboranes. Synthesis in high optical purity of all four possible stereoisomers of .beta.-methylhomoallyl alcoholsJournal of the American Chemical Society, 1986
- A diastereoselective synthesis of both quercus lactone isomers employing allyl-type organometallics as key intermediatesTetrahedron Letters, 1984
- Diene studies. IV. Preparation and protonation of pentadienyllithiumsTetrahedron Letters, 1967
- NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY. THE STRUCTURE OF BUTENYLMAGNESIUM BROMIDE1Journal of the American Chemical Society, 1961