Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 1-2, Pages 107-111Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800606
Keywords
asymmetric catalysis; cycloaddition; hetero-Diels-Alder reaction; oxygen heterocycles; pyridines
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Funding
- Ministerio de Educacion y Ciencia
- FEDER [CTQ 2006-14199/BQU]
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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.
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