학술논문
Chiral Pyrroline-Based Ugi-Three-Component Reactions Are under Kinetic Control.
Document Type
Article
Author
Source
Subject
*CHIRALITY
*KINETIC control
*HETEROCYCLIC compounds
*SUBSTITUTION reactions
*HYDROXYLATION
*
*
*
*
Language
ISSN
1523-7060
Abstract
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. 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. [ABSTRACT FROM AUTHOR]