Journal of Organic Chemistry p. 7674 - 7692 (2015)
Update date:2022-08-15
Topics: -Synthesis -Intramolecular cyclization -Enantiopure -3-Hydroxypiperidines -Sulfinyl Dienyl Amines -Diastereoselective -[2,3]-Sigmatropic Rearrangement
Simal, Carmen
Bates, Robert H.
Urena, Mercedes
Giménez, Irene
Koutsou, Christina
Infantes, Lourdes
Fernández De La Pradilla, Roberto
Viso, Alma
The highly diastereoselective base-promoted intramolecular cyclization of a variety of enantiopure sulfinyl dienyl amines provides novel sulfinyl tetrahydropyridines that are readily converted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement. The influence of N- and C- substituents on the process has been studied. Procedures to shorten the sequence such as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the free amine, under Boc- or ArSO- deprotection conditions have been examined. Good to excellent levels of selectivity are generally observed for the reported transformations (dr: 75/25 to >98/2). A novel protocol to access substituted amino dienyl sulfoxides is also reported.
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