Synthesis of medium-sized cyclic amines by selective ring cleavage of sulfonylated bicyclic amines.
An efficient method of synthesis of functionalized medium-sized cyclic amines (eight- to ten-membered rings) by selective ring opening of sulfonylated bicyclic pyrrolizidine, indolizidine, and quinolizidine compounds is described. The key step is the selective cleavage of the central C-N bond of the bicyclic amine by means of a Julia-like desulfonylation process. Reaction: see text.
Iradier
F
F
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.
Arrayás
R G
RG
Carretero
J C
JC
D000588:Amines / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry; D013450:Sulfones
D000588:Amines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006571:Heterocyclic Compounds; D011763:Pyrrolizidine Alkaloids; D013450:Sulfones; C412858:otonecine