Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation
The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using...
| Main Authors: | , , , |
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| Format: | Journal article |
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Royal Society of Chemistry
2016
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| _version_ | 1797075544049713152 |
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| author | Paton, R Jackson, K Semakul, N Rovis, T |
| author_facet | Paton, R Jackson, K Semakul, N Rovis, T |
| author_sort | Paton, R |
| collection | OXFORD |
| description | The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[c]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules. |
| first_indexed | 2024-03-06T23:51:48Z |
| format | Journal article |
| id | oxford-uuid:72ddb109-ac60-4186-b984-9bd5b592bbe5 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T23:51:48Z |
| publishDate | 2016 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:72ddb109-ac60-4186-b984-9bd5b592bbe52022-03-26T19:52:46ZHeptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activationJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:72ddb109-ac60-4186-b984-9bd5b592bbe5Symplectic Elements at OxfordRoyal Society of Chemistry2016Paton, RJackson, KSemakul, NRovis, TThe diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[c]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules. |
| spellingShingle | Paton, R Jackson, K Semakul, N Rovis, T Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title | Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title_full | Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title_fullStr | Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title_full_unstemmed | Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title_short | Heptamethyl Indenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation |
| title_sort | heptamethyl indenyl ind enables diastereoselective benzamidation of cyclopropenes via rh iii catalyzed c h activation |
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