Aza-<i>ortho</i>-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines
Bandana Singh, Pujan Sasmal, Aaron Taites, Subhadeep Hazra, Jaideep Saha
Abstract
A strategy for activating azabicyclo[1.1.0]butane (ABB) with in situ generated aza- ortho -quinone methide, promoted by HFIP, is reported. This unified activation, vis-à-vis strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the newly installed motif on azetidine nitrogen could be forged into an indoline via Pd-catalyzed hydroamination, leveraging access to medicinally relevant scaffolds.
Topics & Concepts
ChemistryQuinone methideStrain (injury)StereochemistryCombinatorial chemistryQuinoneMedicineInternal medicineSynthesis of β-Lactam CompoundsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis