Two-Component Domino Reactions Initiated from Ketenes: Serendipitous Synthesis of Quinolizidinones Analogous to Chelated Lobeline’s Conformation
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. M...
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| Veröffentlicht in: | Journal of organic chemistry 2015-10, Vol.80 (20), p.10119-10126 |
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| container_end_page | 10126 |
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| container_issue | 20 |
| container_start_page | 10119 |
| container_title | Journal of organic chemistry |
| container_volume | 80 |
| creator | Drège, Emmanuelle Venot, Pierre-Etienne Le Bideau, Franck Retailleau, Pascal Joseph, Delphine |
| description | 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. |
| doi_str_mv | 10.1021/acs.joc.5b01727 |
| format | Article |
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| title | Two-Component Domino Reactions Initiated from Ketenes: Serendipitous Synthesis of Quinolizidinones Analogous to Chelated Lobeline’s Conformation |
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