Related Experiment Video
Updated: Jul 13, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component
Chuo Chen1, Xiaodong Li, Stuart L Schreiber
1Department of Chemistry and Chemical Biology, Howard Hughes Medical Institute, , Institute of Chemistry and Cell Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Abstract:
We report a new catalyst system that should enhance the use of enantioselective 1,3-dipolar cycloadditions of azomethine ylides with electronic-deficient olefins in the divergent pathways of diversity-oriented synthesis (DOS). The underlying reaction is of considerable interest in DOS because its stereospecificity enables stereochemical diversification of up to four tetrahedral centers on pyrrolidine rings. This new catalyst system extends the scope and selectivity of the azomethine ylide cycloaddition and is compatible with reagents used in a one-bead/one-stock solution technology platform for DOS.
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation

