A New Approach to Substituted Cyclobutanes: Direct β-Deprotonation/ Magnesiation of Cyclobutane Carboxamides
- 30 June 2003
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2003 (09) , 1275-1278
- https://doi.org/10.1055/s-2003-40331
Abstract
BuMgN(i-Pr)2 is shown to be kinetically and thermodynamically efficient for deprotonation/magnesiation cis and β to an activating carboxamido group on a cyclobutane ring. The resulting carboxamido-stabilized amido-Grignards are useful reagents. The method provides an entirely new approach to controlled substitution on cyclobutanes. BuMgN(i-Pr)2 will also metalate pivaloyl amides.Keywords
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