New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives
Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moder...
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MDPI AG
2015-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/9/15807 |
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doaj-32505c77d8604d6a9df33e043d2128d92020-11-25T01:28:26ZengMDPI AGMolecules1420-30492015-08-01209158071582610.3390/molecules200915807molecules200915807New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] DerivativesFernando Auria-Luna0Eugenia Marqués-López1Somayeh Mohammadi2Roghayeh Heiran3Raquel P. Herrera4Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, SpainLaboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, SpainHerein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited.http://www.mdpi.com/1420-3049/20/9/15807chiral baseenamineisatylidene malononitrile1,4-dihydropyridineenantioselectiveisatinorganocatalysisspirooxindole2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Fernando Auria-Luna Eugenia Marqués-López Somayeh Mohammadi Roghayeh Heiran Raquel P. Herrera |
| spellingShingle |
Fernando Auria-Luna Eugenia Marqués-López Somayeh Mohammadi Roghayeh Heiran Raquel P. Herrera New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives Molecules chiral base enamine isatylidene malononitrile 1,4-dihydropyridine enantioselective isatin organocatalysis spirooxindole 2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] |
| author_facet |
Fernando Auria-Luna Eugenia Marqués-López Somayeh Mohammadi Roghayeh Heiran Raquel P. Herrera |
| author_sort |
Fernando Auria-Luna |
| title |
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives |
| title_short |
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives |
| title_full |
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives |
| title_fullStr |
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives |
| title_full_unstemmed |
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives |
| title_sort |
new organocatalytic asymmetric synthesis of highly substituted chiral 2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] derivatives |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2015-08-01 |
| description |
Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited. |
| topic |
chiral base enamine isatylidene malononitrile 1,4-dihydropyridine enantioselective isatin organocatalysis spirooxindole 2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] |
| url |
http://www.mdpi.com/1420-3049/20/9/15807 |
| work_keys_str_mv |
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