Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines
The enantioselective 1,3-dipolar cycloaddition between imino esters and (<i>Z</i>)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of t...
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MDPI AG
2022-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/14/4579 |
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| author | Eduardo García-Mingüens Marcos Ferrándiz-Saperas M. de Gracia Retamosa Carmen Nájera Miguel Yus José M. Sansano |
| author_facet | Eduardo García-Mingüens Marcos Ferrándiz-Saperas M. de Gracia Retamosa Carmen Nájera Miguel Yus José M. Sansano |
| author_sort | Eduardo García-Mingüens |
| collection | DOAJ |
| description | The enantioselective 1,3-dipolar cycloaddition between imino esters and (<i>Z</i>)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding <i>cis-</i>2,3-diaminoprolinate. |
| first_indexed | 2024-03-09T06:07:23Z |
| format | Article |
| id | doaj.art-8ad56ceb93e443b6aa72fd4ecb1e9d94 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T06:07:23Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8ad56ceb93e443b6aa72fd4ecb1e9d942023-12-03T12:02:09ZengMDPI AGMolecules1420-30492022-07-012714457910.3390/molecules27144579Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-DiaminopyrrolidinesEduardo García-Mingüens0Marcos Ferrándiz-Saperas1M. de Gracia Retamosa2Carmen Nájera3Miguel Yus4José M. Sansano5Instituto de Síntesis Orgánica (ISO), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica, University of Alicante, P.O. Box 99, 03690 San Vicente del Raspeig, SpainInstituto de Síntesis Orgánica (ISO), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica, University of Alicante, P.O. Box 99, 03690 San Vicente del Raspeig, SpainInstituto de Síntesis Orgánica (ISO), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica, University of Alicante, P.O. Box 99, 03690 San Vicente del Raspeig, SpainCentro de Innovación en Química Avanzada (ORFEO-CINQA), P.O. Box 99, 03690 San Vicente del Raspeig, SpainCentro de Innovación en Química Avanzada (ORFEO-CINQA), P.O. Box 99, 03690 San Vicente del Raspeig, SpainInstituto de Síntesis Orgánica (ISO), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica, University of Alicante, P.O. Box 99, 03690 San Vicente del Raspeig, SpainThe enantioselective 1,3-dipolar cycloaddition between imino esters and (<i>Z</i>)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly applied to the study of the scope of the reaction. The determination of the absolute configuration was evaluated using NMR experiments and electronic circular dichroism (ECD). The reduction and hydrolysis of both groups was performed to generate in an excellent enantiomeric ratio the corresponding <i>cis-</i>2,3-diaminoprolinate.https://www.mdpi.com/1420-3049/27/14/4579nitroprolinatesenantioseletive cycloadditionphosphoramiditeazomethine ylidesdiamines |
| spellingShingle | Eduardo García-Mingüens Marcos Ferrándiz-Saperas M. de Gracia Retamosa Carmen Nájera Miguel Yus José M. Sansano Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines Molecules nitroprolinates enantioseletive cycloaddition phosphoramidite azomethine ylides diamines |
| title | Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines |
| title_full | Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines |
| title_fullStr | Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines |
| title_full_unstemmed | Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines |
| title_short | Enantioselective 1,3-Dipolar Cycloaddition Using (<i>Z</i>)-α-Amidonitroalkenes as a Key Step to the Access to Chiral <i>cis</i>-3,4-Diaminopyrrolidines |
| title_sort | enantioselective 1 3 dipolar cycloaddition using i z i α amidonitroalkenes as a key step to the access to chiral i cis i 3 4 diaminopyrrolidines |
| topic | nitroprolinates enantioseletive cycloaddition phosphoramidite azomethine ylides diamines |
| url | https://www.mdpi.com/1420-3049/27/14/4579 |
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