Palladium-Catalyzed Directed Atroposelective C–H Allylation via β-H Elimination: 1,1-Disubstituted Alkenes as Allyl Surrogates
Bei‐Bei Zhan, Zhen‐Sheng Jia, Jun Luo, Liang Jin, Xufeng Lin, Bing‐Feng Shi
Abstract
Transition-metal-catalyzed dehydrogenative C-H allylation with 1,1-disubstituted alkenes via β-H elimination remains challenging, because of the low reactivity and difficulty of controlling selectivity. Herein, the development of a Pd(II)-catalyzed directed atroposelective C-H allylation with methacrylates is described. Exclusive allylic selectivity was achieved. A vast array of axially chiral biaryl-2-amines are efficiently synthesized with excellent enantioselectivities (up to >99% enantiomeric excess).
Topics & Concepts
ChemistryAllylic rearrangementSelectivityCatalysisPalladiumReactivity (psychology)EnantiomerCombinatorial chemistryMedicinal chemistryOrganic chemistryPathologyAlternative medicineMedicineAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology