{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T19:59:56Z","timestamp":1789934396160,"version":"4.0.1"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"12","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. 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R.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref2\/cit2a","unstructured":"aBlunt, R.; Cooper, D. G.; Porter, R. A.; Wyman, P. A.WO 2009034061, 2009."},{"key":"ref2\/cit2b","unstructured":"bAhmad, N. M.; Lai, J. Y. Q.; Andreotti, D.; Marshall, H. R.; Nash, D. J.; Porter, R. A.WO 2008092876, 2008."},{"key":"ref2\/cit2c","unstructured":"cCoulton, S.; Porter, R. A.WO 2008092872, 2008."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"995","DOI":"10.1002\/cmdc.200700038","volume":"2","author":"Barrow J. C.","year":"2007","journal-title":"ChemMedChem"},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1002\/hlca.19870700129","volume":"70","author":"Seebach D.","year":"1987","journal-title":"Helv. Chim. Acta"},{"key":"ref5\/cit5","unstructured":"For reviews on nitrones and their cycloaddition reactions, see:"},{"key":"ref5\/cit5a","unstructured":"aJones, R. C. F.; Martin, J. N.InSynthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, The Chemistry of Heterocyclic Compounds;Padwa, A.; Pearson, W. H., Eds.Wiley:New York, 2002; Vol. 59, pp1\u221281;"},{"key":"ref5\/cit5b","volume-title":"Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis","author":"Feuer H.","year":"2008"},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"2887","DOI":"10.1021\/cr078371m","volume":"108","author":"Stanley L. M.","year":"2008","journal-title":"Chem. Rev."},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"863","DOI":"10.1021\/cr970324e","volume":"98","author":"Gothelf K. V.","year":"1998","journal-title":"Chem. Rev."},{"key":"ref5\/cit5e","doi-asserted-by":"crossref","first-page":"8042","DOI":"10.1002\/ange.200502640","volume":"117","author":"Cardona F.","year":"2005","journal-title":"Angew. Chem."},{"key":"ref5\/cit5ee","doi-asserted-by":"crossref","first-page":"7832","DOI":"10.1002\/anie.200502640","volume":"44","author":"Cardona F.","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref5\/cit5f","doi-asserted-by":"crossref","first-page":"12247","DOI":"10.1016\/j.tet.2007.09.065","volume":"63","author":"Nair V.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref5\/cit5g","doi-asserted-by":"crossref","first-page":"3235","DOI":"10.1016\/j.tet.2007.01.009","volume":"63","author":"Pellissier H.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref5\/cit5h","doi-asserted-by":"crossref","first-page":"2349","DOI":"10.1055\/s-2006-949626","volume":"15","author":"Bonin M.","year":"2006","journal-title":"Synlett"},{"key":"ref5\/cit5i","doi-asserted-by":"crossref","first-page":"7808","DOI":"10.1002\/chem.200900707","volume":"15","author":"Brandi A.","year":"2009","journal-title":"Chem.\u2014Eur. J."},{"key":"ref6\/cit6","unstructured":"For a review, see:"},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1021\/cr00055a002","volume":"83","author":"Freeman J. P","year":"1983","journal-title":"Chem. Rev."},{"key":"ref6\/cit6b","first-page":"3382","author":"Heaney F.","year":"2001","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"4349","DOI":"10.1016\/S0040-4020(01)00322-2","volume":"57","author":"Friebolin W.","year":"2001","journal-title":"Tetraheron"},{"key":"ref7\/cit7","unstructured":"See recent example of 1,3-dipolar cycloaddition of imidazolone nitrones:"},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1080\/00397910601033781","volume":"37","author":"Cheng S.","year":"2007","journal-title":"Synth. Commun."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"1145","DOI":"10.1016\/j.tetasy.2008.04.006","volume":"19","author":"Aouadi K.","year":"2008","journal-title":"Tetrahedron: Asymmetry"},{"key":"ref7\/cit7c","first-page":"3399","volume":"21","author":"Aouadi K.","year":"2007","journal-title":"Synthesis"},{"key":"ref7\/cit7d","first-page":"3299","volume":"19","author":"Aouadi K.","year":"2006","journal-title":"Synlett"},{"key":"ref7\/cit7e","doi-asserted-by":"crossref","first-page":"1969","DOI":"10.1016\/j.tetasy.2006.06.046","volume":"17","author":"Pernet-Poil-Chevrier A.","year":"2006","journal-title":"Tetrahedron: Asymmetry"},{"key":"ref7\/cit7f","doi-asserted-by":"crossref","first-page":"2694","DOI":"10.1002\/ejoc.200400861","volume":"70","author":"Cantagrel F.","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref7\/cit7g","doi-asserted-by":"crossref","first-page":"1969","DOI":"10.1016\/j.tetasy.2006.06.046","volume":"17","author":"Pernet-Poil-Chevrier A.","year":"2006","journal-title":"Tetrahedron: Asymmetry"},{"key":"ref7\/cit7h","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1021\/ol015743j","volume":"3","author":"Westermann B.","year":"2001","journal-title":"Org. Lett."},{"key":"ref7\/cit7i","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1021\/ol049505a","volume":"6","author":"Baldwin S. W.","year":"2004","journal-title":"Org. Lett."},{"key":"ref8\/cit8","unstructured":"The sterochemistry of10was confirmed by NOESY. Also see ref7a."},{"key":"ref9\/cit9","unstructured":"Possible mechanism to form14"},{"key":"ref10\/cit10","unstructured":"Other solvents (such as toluene, 1,2-dichloroethane, acetonitrile, etc.), bases (such as NaH, KOtBu, etc.), and acids (CF3COOH, CH3COOH, etc.) also work in these reactions. However, these combinations have not been optimized."},{"key":"ref11\/cit11","unstructured":"Possible mechanism to5K:"},{"key":"ref12\/cit12","unstructured":"For other isolated acylaziridines, please see ref6aand the references cited therein."},{"key":"ref13\/cit13","unstructured":"For reviews on reactions of aziridines, see:"},{"key":"ref13\/cit13a","unstructured":"aMitunobu, O. In Comprehensive Organic Synthesis;Trost, B. M.; Fleming, I., Eds. Pergamon:Oxford, UK, 1991; Vol. 6, Chapter1.3."},{"key":"ref13\/cit13b","unstructured":"bPadwa, A. In Comprehensive Organic Synthesis;Trost, B. M.; Fleming, I., Eds. Pergamon:Oxford, UK, 1991; Vol. 4, Chapter4.9."},{"key":"ref13\/cit13c","unstructured":"cThompson, D. J. In Comprehensive Organic Synthesis;Trost, B. M.; Fleming, I., Eds. Pergamon:Oxford, UK, 1991; Vol. 3, Chapter4.1."},{"key":"ref13\/cit13d","unstructured":"dHudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis;Trost, B. M.; Fleming, I., Eds. Pergamon:Oxford, UK, 1991; Vol. 5, Chapter8.1."},{"key":"ref13\/cit13e","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1002\/anie.199405991","volume":"33","author":"Tanner D.","year":"1994","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref14\/cit14","unstructured":"After silica gel chromatograpgy, there is a minor side product (18) isolated (<5%) for entry 2. TheZ-isomer has been comfirmed by COSY and J-resolved HMBC data. This type of side product has been found from other substrates as well."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"2695","DOI":"10.1016\/j.tet.2007.01.010","volume":"63","author":"Inamoto K.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref16\/cit16e","doi-asserted-by":"crossref","first-page":"1833","DOI":"10.1021\/ja044086y","volume":"127","author":"Xin L.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"2314","DOI":"10.1021\/ja0318380","volume":"126","author":"Mattson A. E.","year":"2004","journal-title":"J. Am. Chem. Soc."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol1007923","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,2]],"date-time":"2023-04-02T10:13:07Z","timestamp":1680430387000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol1007923"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,5,19]]},"references-count":46,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2010,6,18]]}},"alternative-id":["10.1021\/ol1007923"],"URL":"https:\/\/doi.org\/10.1021\/ol1007923","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,5,19]]}}}