ChemInform Abstract: Two-Component Domino Reactions Initiated from Ketenes: Serendipitous Synthesis of Quinolizidinones Analogous to Chelated Lobeline′s Conformation

Autor:	Pascal Retailleau, Pierre-Etienne Venot, Franck Le Bideau, Emmanuelle Drège, Delphine Joseph
Rok vydání:	2016
Předmět:	chemistry.chemical_compound Deprotonation Cascade reaction Chemistry Component (thermodynamics) Stereochemistry Sequence (biology) Chelation Lobeline General Medicine Domino Stereocenter
Zdroj:	ChemInform. 47
ISSN:	0931-7597
DOI:	10.1002/chin.201608177
Popis:	An original and efficient synthesis of quinolizidinones through a one-pot two-component cascade reaction of norlobelanine with in situ generated ketenes is reported. Functionalized fused azabicyclic scaffolds bearing multiple stereogenic centers were prepared with excellent diastereoselectivities. Mild optimized conditions involving a key “shuttle base” deprotonation strategy was applied to the synthesis, in a short sequence, of a constrained mimetic of the privileged H-bonded conformation of (−)-lobeline.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c56ac7dac0339b59b3c6b9ce4a381716 https://doi.org/10.1002/chin.201608177 Zobrazit plný text záznamu Plný text