Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction
A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal redu...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2019
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| _version_ | 1797078711577608192 |
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| author | Gabriel, P Gregory, A Dixon, D |
| author_facet | Gabriel, P Gregory, A Dixon, D |
| author_sort | Gabriel, P |
| collection | OXFORD |
| description | A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered indole moiety was triggered. Terminal reduction affords the aza-spiroindoline products in an overall highly chemoselective and diastereoselective one-pot process. |
| first_indexed | 2024-03-07T00:35:39Z |
| format | Journal article |
| id | oxford-uuid:814e2415-d48d-4d4a-bf30-f1ce7a138a2a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:35:39Z |
| publishDate | 2019 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:814e2415-d48d-4d4a-bf30-f1ce7a138a2a2022-03-26T21:29:31ZIridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reactionJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:814e2415-d48d-4d4a-bf30-f1ce7a138a2aEnglishSymplectic Elements at OxfordAmerican Chemical Society2019Gabriel, PGregory, ADixon, DA mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered indole moiety was triggered. Terminal reduction affords the aza-spiroindoline products in an overall highly chemoselective and diastereoselective one-pot process. |
| spellingShingle | Gabriel, P Gregory, A Dixon, D Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title | Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title_full | Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title_fullStr | Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title_full_unstemmed | Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title_short | Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted Pictet–Spengler reaction |
| title_sort | iridium catalyzed aza spirocyclization of indole tethered amides an interrupted pictet spengler reaction |
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