117319-72-9Relevant academic research and scientific papers
Selective Alkylation of Ketones with a Bulky Aluminum Reagent-the THF-TBSOTf System
Saito, Susumu,Ito, Masahiro,Maruoka, Keiji,Yamamoto, Hisashi
, p. 357 - 358 (1997)
Various ketones can be alkylated with tetrahydrofuran (THF) to provide α-siloxybutylated ketones in the presence of a bulky aluminum reagent, lithium diisopropylamide (LDA), and t-butyldimethylsilyl triflate (TBSOTf).
Cleavage of Tetrahydrofuran by tert-Butyldimethylsilyl Iodide and Further Transformations of the Resulting 1-Silyloxy-4-Iodobutane
Nystroem, Jan-Erik,McCanna, Terrence D.,Helquist, Paul,Amouroux, Roger
, p. 56 - 58 (2007/10/02)
Tetrahydrofuran is readily cleaved by tert-butyldimethylsilyl iodide generated in situ by reaction of the chloride with sodium iodide in acetonitrile to give the corresponding 1-silyloxy-4-iodobutane, which in turn undergoes a number of useful functionalizations of the iodo group including substitutions with hetero nucleophiles, such as amine, thiolate sulfinate, and phosphite and carbon nucleophiles such as enolate and acetylide, with survival of the silyloxy group.
