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Description
| - Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68%) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99%ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76%) and with moderate-to-high selectivities (up to 12:1 dr, up to 90%ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts.
- Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68%) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99%ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76%) and with moderate-to-high selectivities (up to 12:1 dr, up to 90%ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts. (en)
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Title
| - Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds
- Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds (en)
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skos:prefLabel
| - Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds
- Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds (en)
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skos:notation
| - RIV/00216208:11310/13:10191191!RIV14-GA0-11310___
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
| - I, P(EE2.3.30.0022), P(GAP207/10/0428), S, Z(MSM0021620857)
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http://linked.open...iv/cisloPeriodika
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/00216208:11310/13:10191191
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - sulfur heterocycles; domino reactions; spiro compounds; organocatalysis (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...odStatuVydavatele
| - GB - Spojené království Velké Británie a Severního Irska
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http://linked.open...ontrolniKodProRIV
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http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...vavai/riv/projekt
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http://linked.open...UplatneniVysledku
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http://linked.open...v/svazekPeriodika
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http://linked.open...iv/tvurceVysledku
| - Císařová, Ivana
- Veselý, Jan
- Remeš, Marek
- Urban, Michal
- Géant, Pierre Yves
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http://linked.open...ain/vavai/riv/wos
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http://linked.open...n/vavai/riv/zamer
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issn
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number of pages
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http://bibframe.org/vocab/doi
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http://localhost/t...ganizacniJednotka
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