Lewis Base-Switched [3 + 3] and [4 + 2] Annulation Reactions of Î-Acetoxy Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of Functionalized α-Pyridyl Acetates and Teraryl Scaffolds
Lewis Base-Switched [3 + 3] and [4 + 2] Annulation Reactions of Î-Acetoxy Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of Functionalized α-Pyridyl Acetates and Teraryl Scaffolds
| dc.contributor.author | Arupula, Sanjeeva K. | |
| dc.contributor.author | Qureshi, Asif Ali | |
| dc.contributor.author | Swamy, K. C.Kumara | |
| dc.date.accessioned | 2022-03-27T09:47:04Z | |
| dc.date.available | 2022-03-27T09:47:04Z | |
| dc.date.issued | 2020-03-20 | |
| dc.description.abstract | Under metal-free conditions, Î-acetoxy allenoates react with cyclic N-sulfonyl imines (sulfamidate imines/sulfonyl imines) to afford functionalized 2-pyridinyl acetates (α-pyridyl acetates) or teraryl motifs by a simple Lewis base switch. Thus, while DBU/Na2CO3 combination-directed [3 + 3] annulation involves sulfonyl elimination via O-S or C-S bond cleavage, affording 2-pyridinyl acetates, Ph3P-catalyzed [4 + 2] annulation leads to functionalized teraryls via Mannich coupling and C-N bond cleavage with retention or cleavage of the sulfamoyloxy group depending on the reaction conditions. | |
| dc.identifier.citation | Journal of Organic Chemistry. v.85(6) | |
| dc.identifier.issn | 00223263 | |
| dc.identifier.uri | 10.1021/acs.joc.9b03281 | |
| dc.identifier.uri | https://pubs.acs.org/doi/10.1021/acs.joc.9b03281 | |
| dc.identifier.uri | https://dspace.uohyd.ac.in/handle/1/13301 | |
| dc.title | Lewis Base-Switched [3 + 3] and [4 + 2] Annulation Reactions of Î-Acetoxy Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of Functionalized α-Pyridyl Acetates and Teraryl Scaffolds | |
| dc.type | Journal. Article | |
| dspace.entity.type |
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