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DyKAT by DiCat: Stereoconvergent Dienamine-Catalyzed Claisen Rearrangements.

Ana De Oliveira Silva¹, Jordan L Harper², Katherine N Fuhr¹

¹Department of Chemistry, Rutgers University-Newark, 73 Warren Street, Newark, New Jersey 07102, United States.

The Journal of Organic Chemistry

|July 26, 2022

Summary

This study demonstrates a novel catalytic method for synthesizing enantioenriched products from γ-epimeric enals using dienamine formation. The developed DyKAT reaction offers a versatile route to valuable pyrrolidine and cyclopentenol compounds.

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Published on: November 27, 2015

Area of Science:

Organic Chemistry
Asymmetric Catalysis

Background:

The Claisen rearrangement is a fundamental carbon-carbon bond-forming reaction.
Developing catalytic asymmetric methods for complex molecule synthesis remains a key challenge.

Purpose of the Study:

To establish the feasibility of a catalytic asymmetric DyKAT reaction for γ-epimeric enals.
To synthesize enantioenriched products via dienamine intermediates.

Main Methods:

Utilized a catalytic asymmetric Claisen rearrangement (DyKAT).
Employed γ-epimeric enals as substrates, including aryl, alkyl, and exocyclic variants.
Isolated and characterized a reactive dienamine intermediate.

Main Results:

Achieved enantioenriched products from diverse γ-epimeric enals.
Demonstrated the formation of quaternary stereocenters.
Successfully converted dienamine intermediates into pyrrolidines and cyclopentenols.
Identified a directing C-H···π interaction governing product stereochemistry.

Conclusions:

The developed DyKAT reaction is a feasible and versatile method for asymmetric synthesis.
The reaction provides access to valuable chiral building blocks.
Understanding transition state interactions is crucial for controlling stereochemistry.