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Direct Synthesis of β-Alkyl N-Aryl Aza Baylis–Hillman Adducts via Nitroso-Ene Reaction

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Department of Chemistry, University of Louisiana at Lafayette, Lafayette, Louisiana 70504, United States
*E-mail: [email protected]
Cite this: J. Org. Chem. 2012, 77, 16, 7119–7123
Publication Date (Web):July 27, 2012
https://doi.org/10.1021/jo301266f
Copyright © 2012 American Chemical Society
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    Abstract

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    A new approach for the direct Fe-catalyzed synthesis of β-alkyl N-aryl aza Baylis–Hillman (ABH) adducts is reported. This approach involves the formation of a C–N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction, which converts allyl esters and carbonyl compounds to novel ABH adducts. A variety of arylhydroxylamines reacted with esters, aldehydes, ketone, and nitriles to yield the corresponding products in moderate to excellent yields.

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    10. Venkata R. Sabbasani, Genping Huang, Yuanzhi Xia, Daesung Lee. Facile Alder-Ene Reactions of Silylallenes Involving an Allenic C(sp 2 )H Bond. Chemistry - A European Journal 2015, 21 (48) , 17210-17214. https://doi.org/10.1002/chem.201503243
    11. David Porter, Belinda M-L Poon, Peter J Rutledge. Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism. Beilstein Journal of Organic Chemistry 2015, 11 , 2549-2556. https://doi.org/10.3762/bjoc.11.275
    12. Jean-Luc Renaud, Sylvain Gaillard. Iron-Catalyzed Carbon–Nitrogen, Carbon–Phosphorus, and Carbon–Sulfur Bond Formation and Cyclization Reactions. 2015, 83-144. https://doi.org/10.1007/3418_2015_103
    13. Siva Murru, Radhey S. Srivastava. Iron‐Catalyzed Allylic C–H Amination of Substituted 1,3‐Dienes. European Journal of Organic Chemistry 2014, 2014 (10) , 2174-2181. https://doi.org/10.1002/ejoc.201301914
    14. V. D. Kiselev, H. A. Kashaeva, L. N. Potapova, D. A. Kornilov, A. I. Konovalov. Ene reaction between 4-phenyl-1,2,4-triazoline-3,5-dione and hex-1-ene. The enthalpies, entropies, and volumes of activation and reaction in solution. Russian Chemical Bulletin 2014, 63 (1) , 280-283. https://doi.org/10.1007/s11172-014-0424-y
    15. Siva Murru, Brandon McGough, Radhey S. Srivastava. Synthesis of substituted quinolines via allylic amination and intramolecular Heck-coupling. Org. Biomol. Chem. 2014, 12 (45) , 9133-9138. https://doi.org/10.1039/C4OB01614A
    16. Siva Murru, August A. Gallo, Radhey S. Srivastava. ChemInform Abstract: Direct Synthesis of β‐Alkyl N‐Aryl Aza Baylis—Hillman Adducts via Nitroso‐Ene Reaction.. ChemInform 2012, 43 (52) https://doi.org/10.1002/chin.201252043
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