- Cleavage of Tetrahydrofuran by tert-Butyldimethylsilyl Iodide and Further Transformations of the Resulting 1-Silyloxy-4-Iodobutane
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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.
- Nystroem, Jan-Erik,McCanna, Terrence D.,Helquist, Paul,Amouroux, Roger
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- SHORT INTRAMOLECULAR DIELS-ALDER APPROACH TO FUNCTIONALIZED SPIRODECANES
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The intramolecular Diels-Alder reaction of a (5'-hexynyl)cyclopentadiene provides a 1,2-tetramethylene-bridged norbornadiene which undergoes selective monohydrogenation followed by ozonolysis to provide the title compounds.
- Nystroem, Jan-E.,McCanna, Terrence D.,Helquist, Paul,Iyer, Ramnath S.
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p. 5393 - 5396
(2007/10/02)
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