Enantiocontrolled Azetidine Library Synthesis via Strain-Release Functionalization of 1-Azabicyclobutanes
Michael Bielecki, Molhm Nassir, Hayden A. Sharma, Nathanyal J. Truax, Nicholas Raheja, Ty M. Thompson, Tamara El‐Hayek Ewing, Bruno Melillo, Benjamin F. Cravatt, Phil S. Baran
Abstract
A simple, modular, and programmable approach to access complex stereopure azetidines through strain-release functionalization is disclosed. The synthetic methods developed enable the parallel synthesis of stereodefined azetidines that would be otherwise laborious to produce. Given the privileged nature of these structures, a set of stereoprobes for use in activity-based protein profiling was prepared and evaluated, revealing proteins in human cancer cells, which were liganded with clear stereo- and chemo-selectivity.
Topics & Concepts
ChemistryAzetidineSurface modificationStrain (injury)StereochemistryCombinatorial chemistryInternal medicinePhysical chemistryMedicineSynthesis and Catalytic ReactionsClick Chemistry and ApplicationsChemical Synthesis and Analysis