Publication

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.

Author

Rijssel E.R. van, Goumans T.P.M., Lodder G., Overkleeft H.S., Marel G.A. van der, Codee J.D.C.

Date

30 May 2013

Links

DOI link

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.