Thiophenol-mediated 1,5-hydrogen transfer for the preparation of pyrrolizidines, indolizidines, and related compounds.
The efficient preparation of 1-azabicyclic alkanes is described. Highly functionalized skeletons are prepared in a concise manner using a radical tin-free 1,5-hydrogen transfer-cyclization process. The precursors for the radical reactions are readily assembled either from pyrrolidine/piperidine/hexahydro-1H-azepine or via condensation of a properly designed N-alkylimine with an allenylzinc species.
Dénès
Fabrice
F
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012-Bern, Switzerland.
Beaufils
Florent
F
Renaud
Philippe
P
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006859:Hydrogen / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D007212:Indolizines; D010636:Phenols; D011763:Pyrrolizidine Alkaloids; D013438:Sulfhydryl Compounds; C500284:hyacinthacine A2; C042983:thiophenol; D006859:Hydrogen