{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:08:00Z","timestamp":1760296080884},"reference-count":19,"publisher":"Elsevier BV","issue":"40","license":[{"start":{"date-parts":[[2001,10,1]],"date-time":"2001-10-01T00:00:00Z","timestamp":1001894400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Tetrahedron Letters"],"published-print":{"date-parts":[[2001,10]]},"DOI":"10.1016\/s0040-4039(01)01433-2","type":"journal-article","created":{"date-parts":[[2003,3,26]],"date-time":"2003-03-26T01:16:11Z","timestamp":1048641371000},"page":"7007-7010","source":"Crossref","is-referenced-by-count":23,"title":["Synthesis of 3-aminopyrrolidines and piperidines from endocyclic enamine derivatives"],"prefix":"10.1016","volume":"42","author":[{"given":"Marta R.P","family":"Norton Matos","sequence":"first","affiliation":[]},{"given":"Carlos A.M","family":"Afonso","sequence":"additional","affiliation":[]},{"given":"Robert A","family":"Batey","sequence":"additional","affiliation":[]}],"member":"78","reference":[{"key":"10.1016\/S0040-4039(01)01433-2_BIB2","doi-asserted-by":"crossref","first-page":"5071","DOI":"10.1016\/S0040-4039(99)00983-1","volume":"40","author":"Chandrasekhar","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB3","doi-asserted-by":"crossref","first-page":"3919","DOI":"10.1021\/jm981026s","volume":"41","author":"Macdonald","year":"1998","journal-title":"J. Med. Chem."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB4","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1016\/S0040-4039(97)10749-3","volume":"39","author":"Langlois","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB5","doi-asserted-by":"crossref","first-page":"3683","DOI":"10.1016\/S0960-894X(98)00667-2","volume":"8","author":"Owens","year":"1998","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB6","doi-asserted-by":"crossref","first-page":"1837","DOI":"10.1016\/S0040-4020(00)00088-0","volume":"56","author":"Christine","year":"2000","journal-title":"Tetrahedron"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB7","doi-asserted-by":"crossref","first-page":"2829","DOI":"10.1021\/jo951482d","volume":"61","author":"Laschat","year":"1996","journal-title":"J. Org. Chem."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB8","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/S0040-4039(96)02301-5","volume":"38","author":"Huang","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB10","doi-asserted-by":"crossref","first-page":"9189","DOI":"10.1016\/S0040-4039(99)01971-1","volume":"40","author":"Norton Matos","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB11","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1039\/a809614g","author":"Batey","year":"1999","journal-title":"Chem. Commun."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB12","doi-asserted-by":"crossref","unstructured":"A similar transformation has been reported on dihydropyrans, using iodonium di-sym-collidine perchlorate [I(sym-Coll)2]ClO4 and benzenesulfonamide, providing stable iodosulfonamides in excellent yields: (a) Danishefsky, S. J.; Koseki, K.; Griffith, D. A.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331\u20138333; (b) Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701\u20135711.","DOI":"10.1021\/ja00047a078"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB13","doi-asserted-by":"crossref","unstructured":"More recently, iodo trifluoracetamide pyran derivatives have been prepared in good yields using NIS and [I(sym-Coll)2]ClO4 in the presence of trifluoracetamide: Erbeck, S.; Prinzbach, H. Tetrahedron Lett. 1997, 38, 2653\u20132656.","DOI":"10.1016\/S0040-4039(97)00448-6"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB14","doi-asserted-by":"crossref","unstructured":"For an example of aziridination of N-tosyl-2-pyrroline, mediated by a manganese nitrido complex, to give N-tosyl-3-trifluoracetamide-2-methoxypyrrolidine, see: Sunose, M.; Anderson, K. M.; Orpen, A. G.; Gallagher, T.; Macdonald, S. J. F. Tetrahedron Lett. 1998, 39, 8885\u20138888.","DOI":"10.1016\/S0040-4039(98)01915-7"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB15","doi-asserted-by":"crossref","unstructured":"For an example of conversion of 3-iodo-2-carbamates to aziridines using KOH\/MeOH, see: Hassner, A.; Heathcock, C. J. Org. Chem. 1964, 29, 3640\u20133645.","DOI":"10.1021\/jo01035a052"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB16","doi-asserted-by":"crossref","unstructured":"For an example of CAN-mediated azidomethoxylation of alkenes, see: Chavan, S. P.; Subbarao, Y. T. Tetrahedron Lett. 1999, 40, 5073\u20135074.","DOI":"10.1016\/S0040-4039(99)00984-3"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB17","doi-asserted-by":"crossref","first-page":"7483","DOI":"10.1016\/0040-4039(95)01603-1","volume":"36","author":"Fujimoto","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB18","doi-asserted-by":"crossref","unstructured":"For a similar example of trans selectivity in N-acyliminium reactions, see: Macdonald, S. J. F.; Clarke, G. D. E.; Dowle, M. D.; Harrison, L. A.; Hodgson, S. T.; Inglis, G. G. A.; Johnson, M. R.; Shah, P.; Upton, R. J.; Walls, S. B. J. Org. Chem. 1999, 64, 5166\u20135175.","DOI":"10.1021\/jo990306s"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB20","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1055\/s-1996-5452","author":"Chiesa","year":"1996","journal-title":"Synlett"},{"key":"10.1016\/S0040-4039(01)01433-2_BIB21","doi-asserted-by":"crossref","first-page":"5315","DOI":"10.1016\/S0040-4039(99)01002-3","volume":"40","author":"Ungureaunu","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/S0040-4039(01)01433-2_BIB22","unstructured":"All new compounds were characterized by IR, 1H, 13C NMR and HRMS. Typical procedures: representative iodocarbamation: A solution of iodine (254 mg, 1 mmol) in dry THF (5 ml) was added dropwise to a stirred solution of N-(benzyloxy)carbonyl-2-pyrroline 1a (n=1) (203 mg, 1 mmol) and tert-butyl carbamate (119 mg, 1 mmol) in dry THF (5 ml) at \u221278\u00b0C and under nitrogen. The resulting mixture was stirred for 10 min and then poured into a cold saturated aqueous solution of NaHCO3 and diethyl ether. The aqueous phase was extracted with diethyl ether (3\u00d710 ml). The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 30:70 EtOAc:hexane) afforded 5a (332 mg, 74%) as an orange foam; Rf=0.46 (30:70 EtOAc:hexane). For entries 2\u20134 further purification is required to remove the excess R1NH2. Representative aziridination: A solution of NaN(SiMe3)2 in THF (0.5 M, 1.46 ml, 0.73 mmol) was added dropwise to a stirred solution of 5a (298 mg, 0.67 mmol) in dry THF (7 ml) and dry methanol (0.35 ml) at \u221278\u00b0C under nitrogen. The mixture was stirred for 5 min at \u221278\u00b0C and then allowed to reach rt. A saturated aqueous solution of NaHCO3 and diethyl ether was then added, and the organic layer separated and the aqueous layer extracted with diethyl ether. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 30:70 EtOAc:hexane) afforded 6a (184 mg, 82%) as a clear oil; Rf=0.30 (20:80 EtOAc:hexane). Representative azido methoxylation: CAN (5.82 g, 10.5 mmol) dissolved in acetonitrile (50 ml) was added dropwise to a cooled (ice-bath) mixture of sodium azide (0.34 g, 5.25 mmol) and 1b (n=2) (0.76 g, 3.5 mmol) in dry acetonitrile (35 ml) and dry methanol (6 ml) under nitrogen. The mixture was gradually brought to rt and stirred overnight. Water and diethyl ether were added and the organic layer separated and washed with ice-cold water. The aqueous layer was extracted once again with diethyl ether, the combined organic layers dried (Na2SO4) and the solvent was removed in vacuo. Purification by column chromatography (SiO2, 10:90 EtOAc:hexane) afforded 7b (0.69 g, 69%) as a clear oil; Rf=0.65 (20:80 EtOAc:hexane)."}],"container-title":["Tetrahedron Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403901014332?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403901014332?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2020,1,12]],"date-time":"2020-01-12T06:30:14Z","timestamp":1578810614000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0040403901014332"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001,10]]},"references-count":19,"journal-issue":{"issue":"40","published-print":{"date-parts":[[2001,10]]}},"alternative-id":["S0040403901014332"],"URL":"https:\/\/doi.org\/10.1016\/s0040-4039(01)01433-2","relation":{},"ISSN":["0040-4039"],"issn-type":[{"value":"0040-4039","type":"print"}],"subject":[],"published":{"date-parts":[[2001,10]]}}}