Sulfoxide-directed enantioselective synthesis of functionalized tetrahydropyridines.
The highly selective base-promoted cyclization of enantiopure sulfinyl dienamines provides stereodefined sulfinyl 1,2,3,6-tetrahydropyridines (dr up to 99:1). Subsequent sigmatropic rearrangement affords tetrahydropyridin-3-ols in good yields and selectivities.
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain, and Instituto de Química Física Rocasolano, IQFR-CSIC , Serrano 119, 28006 Madrid, Spain.
Roberto
R
Fernández de la Pradilla
Carmen
C
Simal
Robert H
RH
Bates
Alma
A
Viso
Lourdes
L
Infantes
D003500:Cyclization; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D011725:Pyridines; D012451:Safrole; C005746:sulfoxide