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...
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Format: | Journal article |
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Royal Society of Chemistry
2016
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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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