A non-nucleophilic Grignard reagent used primarily to add an iso-propyl group to carbonyl groups,1,2 and as a strong base in aprotic solvents.3 An excellent reagent system for non-cryogenic Grignard formation from aryl bromides and iodides bearing sensitive functional groups when combined with the tridentate ligand bis[2-(N,Ndimethylamino) ethyl] ether.4,5,6 Employed in activation of the amine before addition of the ester,7 and synthesis of 3-oxa- and 3-azabicyclo[3.1.0]hexanes from α,β-unsaturated esters.8
References
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2. Synthesis 1977, 18.
3. Pure Appl. Chem. 1980, 21.
4. Org. Lett. 2006, 8, 305
5. Org. Lett. 2006, 8, 3141.
6. Org. Lett. 2005, 7, 5593.
7. J. Prakt. Chem. 1997, 339, 517.
8. Tetrahedron Lett. 2010, 51, 1955.