Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis
We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-<i>endo</i>-dig and a 8-<i>endo</i>-dig, followed with a Grob-type fragmentation and a hetero Di...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/21/4976 |
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doaj-f182694021b749a39ee0df126bb91c362020-11-25T03:52:36ZengMDPI AGMolecules1420-30492020-10-01254976497610.3390/molecules25214976Gold(I)-Catalyzed Domino Reaction for Furopyrans SynthesisMarie Ruch0Nicolas Brach1Roméric Galéa2Patrick Wagner3Gaëlle Blond4Laboratoire d’Innovation Thérapeutique, Université de Strasbourg, CNRS, UMR 7200, 67000 Strasbourg, FranceLaboratoire d’Innovation Thérapeutique, Université de Strasbourg, CNRS, UMR 7200, 67000 Strasbourg, FranceLaboratoire d’Innovation Thérapeutique, Université de Strasbourg, CNRS, UMR 7200, 67000 Strasbourg, FranceLaboratoire d’Innovation Thérapeutique, Université de Strasbourg, CNRS, UMR 7200, 67000 Strasbourg, FranceLaboratoire d’Innovation Thérapeutique, Université de Strasbourg, CNRS, UMR 7200, 67000 Strasbourg, FranceWe report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-<i>endo</i>-dig and a 8-<i>endo</i>-dig, followed with a Grob-type fragmentation and a hetero Diels–Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed.https://www.mdpi.com/1420-3049/25/21/4976gold(I)-catalysisdomino reactionselectrocyclizationheterocycleshetero Diels–Alderfuropyrans |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Marie Ruch Nicolas Brach Roméric Galéa Patrick Wagner Gaëlle Blond |
| spellingShingle |
Marie Ruch Nicolas Brach Roméric Galéa Patrick Wagner Gaëlle Blond Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis Molecules gold(I)-catalysis domino reactions electrocyclization heterocycles hetero Diels–Alder furopyrans |
| author_facet |
Marie Ruch Nicolas Brach Roméric Galéa Patrick Wagner Gaëlle Blond |
| author_sort |
Marie Ruch |
| title |
Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis |
| title_short |
Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis |
| title_full |
Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis |
| title_fullStr |
Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis |
| title_full_unstemmed |
Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis |
| title_sort |
gold(i)-catalyzed domino reaction for furopyrans synthesis |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2020-10-01 |
| description |
We report herein an efficient synthesis of furopyran derivatives through a gold(I)-catalyzed domino reaction. The cascade reaction starts with two regioselective cyclizations, a 5-<i>endo</i>-dig and a 8-<i>endo</i>-dig, followed with a Grob-type fragmentation and a hetero Diels–Alder. The obtained furopyran derivatives contain fused and spiro-heterocycles. During this one-pot process, four bonds and four controlled stereogenic centers including a quaternary center are formed. |
| topic |
gold(I)-catalysis domino reactions electrocyclization heterocycles hetero Diels–Alder furopyrans |
| url |
https://www.mdpi.com/1420-3049/25/21/4976 |
| work_keys_str_mv |
AT marieruch goldicatalyzeddominoreactionforfuropyranssynthesis AT nicolasbrach goldicatalyzeddominoreactionforfuropyranssynthesis AT romericgalea goldicatalyzeddominoreactionforfuropyranssynthesis AT patrickwagner goldicatalyzeddominoreactionforfuropyranssynthesis AT gaelleblond goldicatalyzeddominoreactionforfuropyranssynthesis |
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1724481958490144768 |