- A metathetical cycloaddition-cycloreversion approach to the formation of furan scaffold libraries
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A general cycloaddition-cycloreversion metathesis procedure for the selective formation of a furan-based template-directed scaffold is described. In addition, features relative to library construction, such as the chemoselective nature of dipole formation, are discussed. Through the investigation of the temperature sensitive cleavage step, the furan synthesis was found to be accelerated by aqueous medium at physiological temperature leading to pure product from the solid-phase under biologically relevant conditions. The chemoselective nature of the rhodium(II) mediated cycloaddition allowed the selective formation of a key dipole intermediate, in the presence of a number of carbene-active functional groups, to facilitate the split-pool combinatorial synthesis of a small library of compounds. Copyright (C) 1998 Elsevier Science Ltd.
- Whitehouse, Darren L.,Nelson Jr., Kingsley H.,Savinov, Sergey N.,Loewe, Ralf S.,Austin, David J.
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p. 1273 - 1282
(2007/10/03)
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- Cationic Carbon to Nitrogen Rearrangements in the Reactions of N-(Sulfonyloxy)amines with Aldehydes
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A series of aromatic and aliphatic aldehydes was reacted with N-((p-nitrobenzenesulfonyl)oxy)methylamine in chloroform.Products resulting from both carbon migration and hydride migration to nitrogen were isolated.The ratios of carbon to hydride migration products were used to clarify the reaction mechanism.The results support a two-step process in which cationic carbon to nitrogen rearrangements is rate determining.
- Hoffman, Robert V.,Salvador, James M.
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p. 4487 - 4490
(2007/10/02)
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