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Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.

Justin M Lopchuk¹, Kasper Fjelbye¹, Yu Kawamata¹

¹Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|February 1, 2017

Summary

This summary is machine-generated.

Medicinal chemists can now easily install strained rings like bicyclo[1.1.1]pentane in drug discovery using a new strain-release strategy. This method allows for "any-stage" functionalization, simplifying the synthesis of complex molecules.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Drug Discovery

Background:

Drug discovery increasingly utilizes strained bioisosteres (e.g., bicyclo[1.1.1]pentane, azetidine, cyclobutane) to explore novel chemical space.
The synthetic challenge of incorporating these strained fragments often hinders their application in lead compound modification.

Purpose of the Study:

To develop a general strategy for the facile, "any-stage" installation of small, strained ring systems.
To introduce a novel stereospecific strain-release reaction for functionalizing heteroatoms with strained rings.

Main Methods:

Development of a general strategy utilizing spring-loaded, strained C-C and C-N bonds reacting with nucleophiles.
Application of the methodology to small building blocks, late-stage intermediates, bioconjugation, and peptide labeling.
Synthesis and characterization of four new chiral "cyclopentylation" reagents.

Main Results:

Demonstrated "any-stage" installation of strained rings, overcoming previous synthetic hurdles.
Achieved the first stereospecific strain-release functionalization of amines, alcohols, thiols, and carboxylic acids.
Successfully applied the methodology to bioconjugation and peptide labeling.

Conclusions:

The developed strain-release strategy provides a versatile and efficient method for incorporating strained rings in medicinal chemistry.
This approach significantly expands the synthetic accessibility of strained bioisosteres for drug discovery and chemical biology applications.