Functionalisation of isoindolinones via a calcium catalysed Hosomi-Sakurai allylation
A rapid and functionally tolerant calcium catalysed Hosomi-Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be synthesised in high yields and the reaction is shown to be tolerant to a range of medicinally relevant functional groups including heterocycles. Th...
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| Published in | Chemical communications (Cambridge, England) Vol. 55; no. 57; pp. 8317 - 8320 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
11.07.2019
Royal Society of Chemistry |
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| Online Access | Get full text |
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| Abstract | A rapid and functionally tolerant calcium catalysed Hosomi-Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be synthesised in high yields and the reaction is shown to be tolerant to a range of medicinally relevant functional groups including heterocycles. The synthetic utility of the reaction has been shown, and a plausible reaction mechanism is provided. |
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| AbstractList | A rapid and functionally tolerant calcium catalysed Hosomi–Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be synthesised in high yields and the reaction is shown to be tolerant to a range of medicinally relevant functional groups including heterocycles. The synthetic utility of the reaction has been shown, and a plausible reaction mechanism is provided. |
| Author | Basson, Ashley J. McLaughlin, Mark G. |
| Author_xml | – sequence: 1 givenname: Ashley J. surname: Basson fullname: Basson, Ashley J. organization: Manchester Metropolitan Univ, Dept Nat Sci, Fac Sci & Engn, Chester St, Manchester M1 5GD, Lancs, England – sequence: 2 givenname: Mark G. orcidid: 0000-0002-5999-4703 surname: McLaughlin fullname: McLaughlin, Mark G. email: m.mclaughlin@mmu.ac.uk organization: Manchester Metropolitan Univ, Dept Nat Sci, Fac Sci & Engn, Chester St, Manchester M1 5GD, Lancs, England |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31257381$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_tet_2022_132764 crossref_primary_10_1002_adsc_202200237 crossref_primary_10_1016_j_xcrp_2022_101234 crossref_primary_10_1002_cssc_202100225 crossref_primary_10_1002_ejoc_202100400 crossref_primary_10_1016_j_ccr_2023_215140 crossref_primary_10_1039_D2RA02720H crossref_primary_10_1021_acs_joc_0c00482 crossref_primary_10_1039_D2OB01663J crossref_primary_10_1002_adsc_202100522 crossref_primary_10_2174_1385272827666221212163027 crossref_primary_10_1002_ejoc_202300452 crossref_primary_10_1002_adsc_202300917 crossref_primary_10_1002_chem_202201107 |
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| Keywords | EFFICIENT SYNTHESIS ISOINDOLIN-1-ONES LACTAMS ASYMMETRIC-SYNTHESIS CYCLIZATION RUCL2(=CHR)(PR) |
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| Snippet | A rapid and functionally tolerant calcium catalysed Hosomi-Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be... A rapid and functionally tolerant calcium catalysed Hosomi–Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be... |
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| SubjectTerms | Allyl compounds Calcium Chemical reactions Chemistry Chemistry, Multidisciplinary Functional groups Physical Sciences Reaction mechanisms Science & Technology |
| Title | Functionalisation of isoindolinones via a calcium catalysed Hosomi-Sakurai allylation |
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