6533b826fe1ef96bd1284588
RESEARCH PRODUCT
Highly Enantio- and Diastereoselective Inverse Electron Demand Hetero-Diels-Alder Reaction using 2-Alkenoylpyridine N-Oxides as Oxo-Heterodienes
Santiago BarrosoM. Carmen MuñozGonzalo BlayJosé R. Pedrosubject
chemistry.chemical_compoundchemistryPyridineEnantioselective synthesisOrganic chemistryReactivity (chemistry)General ChemistryElectronRing (chemistry)CycloadditionCatalysisDiels–Alder reactiondescription
A general catalytic inverse electron demand hetero-Diels Alder reaction for 2-alkenoylpyridine N-oxides is presented. 2-Alkenoylpyridine N-oxides react very efficiently with alkenes in the presence of bisoxazolidine-copper(II) [BOX-Cu(II)] complexes to give chiral dihydropyrans bearing a pyridine ring at the 6-position with very high yields and excellent diastereo- and enantioselectivity. These heterodienes exhibited higher reactivity and enantioselectivity than the corresponding non-oxidized 2-alkenoylpyridines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-12-19 | Advanced Synthesis & Catalysis |