Tuning the reactivity of O-tert-butyldimethylsilylimidazolyl aminals towards organolithium reagents
T Gimisis, P Arsenyan, D Georganakis, L Leondiadis
Index: Gimisis, Thanasis; Arsenyan, Pavel; Georganakis, Dimitris; Leondiadis, Leondios Synlett, 2003 , # 10 p. 1451 - 1454
Full Text: HTML
Citation Number: 8
Abstract
Abstract O-tert-Butyldimethylsilylimidazolyl aminals are N, O-acetals that form readily from aldehydes, and although they function as aldehyde stabilizing and protecting groups under various conditions, we report here that they react with organolithium reagents similarly to the parent aldehydes. The mechanism involves the intermediate formation of a 2-imidazolyl anion as is exemplified by the isolation of 2-TBDMS-imidazole. Substitution of the ...
Related Articles:
[Caycho, Juana Robles; Tellado, Fernando Garcia; De Armas, Pedro; Tellado, Jose Juan Marrero Tetrahedron Letters, 1997 , vol. 38, # 2 p. 277 - 280]
A new access to acyl-and aroyllithiums via lithium-tellurium exchange
[Journal of the American Chemical Society, , vol. 112, # 1 p. 455 - 457]
Tuning the reactivity of O-tert-butyldimethylsilylimidazolyl aminals towards organolithium reagents
[Synlett, , # 10 p. 1451 - 1454]
Solvent effects on the rates of solvolysis of pinacolyl derivatives
[Roberts, Donald D.; Hall, Edward W. Journal of Organic Chemistry, 1988 , vol. 53, # 11 p. 2573 - 2579]
[Chemistry - A European Journal, , vol. 7, # 14 p. 3043 - 3051]