doi: 10.1021/ol9025759.
Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of 2-allyloxypyridines and related heterocycles
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- PMID: 20017518
- DOI: 10.1021/ol9025759
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Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of 2-allyloxypyridines and related heterocycles
Org Lett.
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Abstract
Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of (E)- and (Z)-allyloxy substituted N-heterocycles generates N-allyl N-heterocyclic amides in good yields and high enantioselectivities (up to 96% ee). The chiral palladacycle COP-Cl (5 mol %) is used as a catalyst with silver(I) trifluoroacetate (10 mol %) at 35-45 degrees C. Examples of heterocycles synthesized include 2-pyridones, quinolin-2(1H)-ones, and isoquinolin-1(2H)-ones.
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