Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines
Addressing the asymmetric synthesis of oxindole-based α-aminoboronic acids, instead of the expected products we disclosed the efficient homocoupling of oxindole-based N-tert-butanesulfinyl imines, with the generation of chiral, quaternary 1,2-diamines in a mild and completely stereoselective way. Th...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.34 |
| _version_ | 1819120551892877312 |
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| author | Marco Manenti Leonardo Lo Presti Giorgio Molteni Alessandra Silvani |
| author_facet | Marco Manenti Leonardo Lo Presti Giorgio Molteni Alessandra Silvani |
| author_sort | Marco Manenti |
| collection | DOAJ |
| description | Addressing the asymmetric synthesis of oxindole-based α-aminoboronic acids, instead of the expected products we disclosed the efficient homocoupling of oxindole-based N-tert-butanesulfinyl imines, with the generation of chiral, quaternary 1,2-diamines in a mild and completely stereoselective way. The obtained 3,3′-bisoxindole derivatives were fully characterized by NMR and single-crystal X-ray diffraction analysis and proved to be single diastereoisomers and atropisomers. A plausible mechanism for the one-pot Cu(II)-catalyzed Bpin addition to the isatin-derived ketimine substrate and subsequent homocoupling is described. |
| first_indexed | 2024-12-22T06:22:28Z |
| format | Article |
| id | doaj.art-f0e6b4abae70475aa3cd9e55ae28b46f |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T06:22:28Z |
| publishDate | 2022-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f0e6b4abae70475aa3cd9e55ae28b46f2022-12-21T18:35:55ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-03-0118130330810.3762/bjoc.18.341860-5397-18-34Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin iminesMarco Manenti0Leonardo Lo Presti1Giorgio Molteni2Alessandra Silvani3Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano, 20133, ItalyDipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano, 20133, ItalyDipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano, 20133, ItalyDipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano, 20133, ItalyAddressing the asymmetric synthesis of oxindole-based α-aminoboronic acids, instead of the expected products we disclosed the efficient homocoupling of oxindole-based N-tert-butanesulfinyl imines, with the generation of chiral, quaternary 1,2-diamines in a mild and completely stereoselective way. The obtained 3,3′-bisoxindole derivatives were fully characterized by NMR and single-crystal X-ray diffraction analysis and proved to be single diastereoisomers and atropisomers. A plausible mechanism for the one-pot Cu(II)-catalyzed Bpin addition to the isatin-derived ketimine substrate and subsequent homocoupling is described.https://doi.org/10.3762/bjoc.18.34atropoisomerbis(pinacolato)diboron3,3′-bisoxindolen-tert-butanesulfinyl ketiminehomocoupling |
| spellingShingle | Marco Manenti Leonardo Lo Presti Giorgio Molteni Alessandra Silvani Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines Beilstein Journal of Organic Chemistry atropoisomer bis(pinacolato)diboron 3,3′-bisoxindole n-tert-butanesulfinyl ketimine homocoupling |
| title | Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines |
| title_full | Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines |
| title_fullStr | Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines |
| title_full_unstemmed | Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines |
| title_short | Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines |
| title_sort | unexpected chiral vicinal tetrasubstituted diamines via borylcopper mediated homocoupling of isatin imines |
| topic | atropoisomer bis(pinacolato)diboron 3,3′-bisoxindole n-tert-butanesulfinyl ketimine homocoupling |
| url | https://doi.org/10.3762/bjoc.18.34 |
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