Iridium-catalyzed asymmetric -selective hydrogenation of 1,3-disubstituted isoquinolines
The development of the first asymmetric trans -selective hydrogenation of 1,3-disubstituted isoquinolines is reported. Utilizing [Ir(cod)Cl] 2 and a commercially available chiral Josiphos ligand, a variety of differentially substituted isoquinolines are hydrogenated to produce enantioenriched trans...
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| Published in: | Chemical science (Cambridge) Vol. 13; no. 11; pp. 3227 - 3232 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Published: |
16-03-2022
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| Online Access: | Get full text |
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| Summary: | The development of the first asymmetric
trans
-selective hydrogenation of 1,3-disubstituted isoquinolines is reported. Utilizing [Ir(cod)Cl]
2
and a commercially available chiral Josiphos ligand, a variety of differentially substituted isoquinolines are hydrogenated to produce enantioenriched
trans
-tetrahydroisoquinolines in good yield with high levels of enantioselectivity. Directing group studies demonstrate that the hydroxymethyl functionality at the C1 position is critical for hydrogenation to favor the
trans
-diastereomer. Preliminary mechanistic studies reveal that non-coordinating chlorinated solvents and halide additives are crucial to enable
trans
-selectivity.
trans
-Selective asymmetric hydrogenation of 1,3-disubstituted isoquinolines. |
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| Bibliography: | Electronic supplementary information (ESI) available. CCDC 10.1039/d1sc06729j For ESI and crystallographic data in CIF or other electronic format see DOI 2120281 |
| ISSN: | 2041-6520 2041-6539 |
| DOI: | 10.1039/d1sc06729j |