Chiral Pyrroline-Based Ugi-Three-Component Reactions Are under Kinetic Control
Although it is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and computational evidence that Ugi reactions on hydroxylated pyrrolines proceed under kinetic control is reported.
- Rijssel E.R. van, Goumans T.P.M., Lodder G., Overkleeft H.S., Marel G.A. van der, Codee J.D.C.
- 30 May 2013
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The stereochemistry of the reaction is established with the addition of the isocyanide to the intermediate iminium ion, whose conformation is determined by its substitution pattern.