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- Title
Intramolecular [2+2] Cycloaddition of N‐Allylcinnamamines and N‐Allylcinnamamides by Visible‐Light Photocatalysis.
- Authors
Oderinde, Martins S.; Kempson, James; Smith, Daniel; Meanwell, Nicholas A.; Mao, Edna; Pawluczyk, Joseph; Vetrichelvan, Muthalagu; Pitchai, Manivel; Karmakar, Ananta; Rampulla, Richard; Li, Jianqing; Murali Dhar, T. G.; Mathur, Arvind
- Abstract
The visible light‐promoted intramolecular [2+2] cycloaddition of N‐allylcinnamamines and N‐allylcinnamamides in the presence of catalytic amounts of [Ir{dF(CF3)ppy}2(dtbpy)]PF6 is reported. Low energy visible light and a high triplet energy iridium‐photosensitizer were efficient at promoting the cycloaddition reaction of N‐allylcinnamamides and N‐allylcinnamamines to the corresponding aryl‐3‐azabicyclo[3.2.0]heptanones and aryl‐3‐azabicyclo[3.2.0]heptanes, respectively, with high diastereoselectivity and under mild conditions. Azabicyclic fused rings have been employed as surrogates for piperidine motifs in drug discovery. Functional groups useful for deployment and/or elaboration in drug discovery campaigns were all shown to be tolerated, including halides, CF3, cyanide, ester, acetamide, acetate, CH3O, pyridyl, furan, carbamate, tosyl, benzyl, and benzoate.
- Subjects
RING formation (Chemistry); PHOTOCATALYSIS; VISIBLE spectra; FUNCTIONAL groups; HEPTANE; BENZOATES; ACETAMIDE
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 1, p41
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201901482