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Diastereoselective synthesis of quinolizidin-4-one and indolizidin-3-one derivatives with a spirocyclic motif via cascade cyclization using a gold(I)/Brønsted acid relay catalysis
- Source :
- Tetrahedron Letters. 56:6266-6268
- Publication Year :
- 2015
- Publisher :
- Elsevier BV, 2015.
-
Abstract
- Functionalized quinolizidin-4-ones and indolizidin-3-ones were synthesized from mixed N,O-acetals with a terminal alkyne unit and nucleophiles with two reactive sites by a gold(I)/Bronsted acid relay catalysis with 40–90% yield. The reactions are proposed to proceed through gold-catalyzed carboalkoxylation of the alkynes with the internal mixed N,O-acetals, giving the corresponding cyclic enols, which are transformed to spirocyclic compounds by a Bronsted acid catalyst. The latter spirocyclization process occurs under thermodynamic control, providing polycyclic quinolizidin-4-one and indolizidin-3-one derivatives diastereoselectively.
Details
- ISSN :
- 00404039
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........33762a42a8bf4ef074fa7042e182e38f