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Volumn 68, Issue 22, 2012, Pages 4067-4105

Methods for direct alkene diamination, new & old

Author keywords

1,2 Diamine; 1,2 Diaminoalkane; 1,2 Diazide; Alkene; Aminoauration; Aminocupration; Aminomercuration; Aminopalladation; Aminothallation; Bis azidonation; Bisnitration; Catalysis; Cycloguanidination; Diamination; Diaziridinone; Dinitrogen tetroxide; Dinitrogen trioxide; Guanidine; Hypervalent iodine; Imidazolidinone; Imidazolination; Iodane; Iodine azide; Iodonium; Nitroamination; Nitrogen dioxide; Nitrogen oxide; Nitrosylation; Organocatalysis; Pseudonitrosite; Sulfamide

Indexed keywords

2,3 DIAMINOPROPIONIC ACID; ACETONITRILE; ALANINE DERIVATIVE; ALKENE; AMIDE; AMMONIUM NITRATE; CAPREOMYCIN; DIAMINE DERIVATIVE; DIAMINO ACID; ETHAMBUTOL; FERROUS ION; HALOGEN; HEAVY METAL; IODINE; LEAD; LITHIUM; MERCURY; MOXIFLOXACIN; NITROGEN DIOXIDE; NITROGEN OXIDE; OSELTAMIVIR; QUINOLINE DERIVED ANTIINFECTIVE AGENT; QUISQUALIC ACID; REAGENT; SODIUM NITRITE; STILBENE DERIVATIVE; SULFONAMIDE; THALLIUM; UNINDEXED DRUG; ZANAMIVIR;

EID: 84860474752     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.036     Document Type: Review
Times cited : (137)

References (412)
  • 1
    • 33745110538 scopus 로고    scopus 로고
    • For a review detailing the biological relevance of 1,2-diamines and their derivatives, see:, See also Refs. 7 and 35
    • For a review detailing the biological relevance of 1,2-diamines and their derivatives, see: S.R.S. Saibabu Kotti, C. Timmons, and G. Li Chem. Biol. Drug Des. 67 2006 101 114 See also Refs. 7 and 35
    • (2006) Chem. Biol. Drug Des. , vol.67 , pp. 101-114
    • Saibabu Kotti, S.R.S.1    Timmons, C.2    Li, G.3
  • 3
    • 0000567366 scopus 로고
    • B.M. Trost, I. Fleming, S.V. Ley, Pergamon Oxford
    • J.E.G. Kemp B.M. Trost, I. Fleming, S.V. Ley, Comprehensive Organic Synthesis Vol. 7 1991 Pergamon Oxford 488
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 488
    • Kemp, J.E.G.1
  • 66
    • 80052785689 scopus 로고    scopus 로고
    • For a comprehensive review of the preparation of conformationally restricted diamines and their importance in drug design, see
    • For a comprehensive review of the preparation of conformationally restricted diamines and their importance in drug design, see: O.O. Grygorenko, D.S. Radchenko, D.M. Volochnyuk, A.A. Tolmachev, and I.V. Komarov Chem. Rev. 111 2011 5506 5568
    • (2011) Chem. Rev. , vol.111 , pp. 5506-5568
    • Grygorenko, O.O.1    Radchenko, D.S.2    Volochnyuk, D.M.3    Tolmachev, A.A.4    Komarov, I.V.5
  • 76
    • 70349095283 scopus 로고    scopus 로고
    • J. Magano Chem. Rev. 109 2009 4398 4438
    • (2009) Chem. Rev. , vol.109 , pp. 4398-4438
    • Magano, J.1
  • 123
    • 0003299714 scopus 로고
    • For a review of these early studies, see
    • For a review of these early studies, see: J.L. Riebsomer Chem. Rev. 36 1945 157 233
    • (1945) Chem. Rev. , vol.36 , pp. 157-233
    • Riebsomer, J.L.1
  • 157
  • 214
    • 84886158010 scopus 로고    scopus 로고
    • Radical Chemistry with Azides
    • For a recent review of the radical chemistry of the azide anion and organoazides, see: S. Brase, K. Banert, John Wiley & Sons Chichester, UK
    • For a recent review of the radical chemistry of the azide anion and organoazides, see: C. Jimeno, and P. Renaud Radical Chemistry with Azides S. Brase, K. Banert, Organic Azides: Syntheses and Applications 2010 John Wiley & Sons Chichester, UK 239 267
    • (2010) Organic Azides: Syntheses and Applications , pp. 239-267
    • Jimeno, C.1    Renaud, P.2
  • 216
    • 4243870790 scopus 로고
    • For a review of free-radical redox addition to alkenes, including diazidonation, see
    • For a review of free-radical redox addition to alkenes, including diazidonation, see: F. Minisci Acc. Chem. Res. 8 1975 165 171
    • (1975) Acc. Chem. Res. , vol.8 , pp. 165-171
    • Minisci, F.1
  • 222
    • 31544432330 scopus 로고    scopus 로고
    • For a recent application of Fristad's methodology, see
    • For a recent application of Fristad's methodology, see: T. Suzuki, A. Shibata, N. Morohashi, and Y. Ohba Chem. Lett. 34 2005 1476 1477
    • (2005) Chem. Lett. , vol.34 , pp. 1476-1477
    • Suzuki, T.1    Shibata, A.2    Morohashi, N.3    Ohba, Y.4
  • 228
    • 33947574424 scopus 로고
    • For a review, see
    • For a review, see: E. Zbiral Synthesis 1972 285 302
    • (1972) Synthesis , pp. 285-302
    • Zbiral, E.1
  • 247
    • 62549088340 scopus 로고    scopus 로고
    • For a recent review of methods for imidazoline synthesis, see
    • For a recent review of methods for imidazoline synthesis, see: H. Liu, and D.M. Du Adv. Synth. Catal. 351 2009 489 519
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 489-519
    • Liu, H.1    Du, D.M.2
  • 253
    • 34250829680 scopus 로고    scopus 로고
    • For an overview of this mechanism and the aminohalogenation reaction, see
    • For an overview of this mechanism and the aminohalogenation reaction, see: G. Li, S.R.S.S. Kotti, and C. Timmons Eur. J. Org. Chem. 2007 2745 2758
    • (2007) Eur. J. Org. Chem. , pp. 2745-2758
    • Li, G.1    Kotti, S.R.S.S.2    Timmons, C.3
  • 262
    • 77949827603 scopus 로고    scopus 로고
    • For use of this methodology in the preparation of iminocyclitols, see
    • For use of this methodology in the preparation of iminocyclitols, see: M. Ganesan, R.V. Madhukarrao, and N.G. Ramesh Org. Biomol. Chem. 8 2010 1527 1530
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 1527-1530
    • Ganesan, M.1    Madhukarrao, R.V.2    Ramesh, N.G.3
  • 270
    • 22144490556 scopus 로고    scopus 로고
    • For diamination through sequential azidoiodination and displacement of the iodide with azide, see
    • For diamination through sequential azidoiodination and displacement of the iodide with azide, see: H.R. Pfaendler, and A. Klingl Helv. Chim. Acta 88 2005 1486 1490
    • (2005) Helv. Chim. Acta , vol.88 , pp. 1486-1490
    • Pfaendler, H.R.1    Klingl, A.2
  • 282
    • 0027379212 scopus 로고
    • For a review of alkene co-halogenation, see
    • For a review of alkene co-halogenation, see: J. Rodriguez, and J.P. Dulcére Synthesis 1993 1177 1205
    • (1993) Synthesis , pp. 1177-1205
    • Rodriguez, J.1    Dulcére, J.P.2
  • 301
    • 8644274671 scopus 로고    scopus 로고
    • See also
    • See also: M. Shen, and C. Li J. Org. Chem. 69 2004 7906 7909
    • (2004) J. Org. Chem. , vol.69 , pp. 7906-7909
    • Shen, M.1    Li, C.2
  • 305
    • 3042851809 scopus 로고    scopus 로고
    • For a review of iodine-mediated alkene diazidonation, see
    • For a review of iodine-mediated alkene diazidonation, see: G. Koser Top. Curr. Chem. 224 2003 137 172
    • (2003) Top. Curr. Chem. , vol.224 , pp. 137-172
    • Koser, G.1
  • 336
    • 0037459884 scopus 로고    scopus 로고
    • For an illustration of this chemical stability, see
    • For an illustration of this chemical stability, see: K. Muñiz Tetrahedron Lett. 44 2003 3547 3549
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3547-3549
    • Muñiz, K.1
  • 340
    • 28144436808 scopus 로고    scopus 로고
    • For a detailed account of these efforts, see
    • For a detailed account of these efforts, see: K. Muñiz New J. Chem. 29 2005 1371 1385
    • (2005) New J. Chem. , vol.29 , pp. 1371-1385
    • Muñiz, K.1
  • 341
    • 2942609661 scopus 로고    scopus 로고
    • For theoretical studies, see
    • For theoretical studies, see: D.V. Deubel, and K. Muñiz Chem. - Eur. J. 10 2004 2475 2486
    • (2004) Chem. - Eur. J. , vol.10 , pp. 2475-2486
    • Deubel, D.V.1    Muñiz, K.2
  • 346
    • 34250780396 scopus 로고    scopus 로고
    • For an informative introduction to the process of alkene aminopalladation, see
    • For an informative introduction to the process of alkene aminopalladation, see: A. Minatti, and K. Muñiz Chem. Soc. Rev. 36 2007 1142 1152
    • (2007) Chem. Soc. Rev. , vol.36 , pp. 1142-1152
    • Minatti, A.1    Muñiz, K.2
  • 357
    • 68149157234 scopus 로고    scopus 로고
    • DFT calculations conducted by Lin and co-workers suggest, contrary to experimental evidence, that diamination in this case may proceed through a sequence of anti-aminopalladation and direct reductive elimination from the Pd(IV) intermediate
    • DFT calculations conducted by Lin and co-workers suggest, contrary to experimental evidence, that diamination in this case may proceed through a sequence of anti-aminopalladation and direct reductive elimination from the Pd(IV) intermediate: H.Z. Yu, Y. Fu, Q.X. Guo, and Z.Y. Lin Organometallics 28 2009 4507 4510
    • (2009) Organometallics , vol.28 , pp. 4507-4510
    • Yu, H.Z.1    Fu, Y.2    Guo, Q.X.3    Lin, Z.Y.4
  • 367
    • 84857203983 scopus 로고    scopus 로고
    • Muñiz and co-workers have most recently reported the use of palladium catalysis for the intramolecular diamination of acrylic esters using sulfamates as the nitrogen source
    • Muñiz and co-workers have most recently reported the use of palladium catalysis for the intramolecular diamination of acrylic esters using sulfamates as the nitrogen source: P. Chávez, J. Kirsch, J. Streuff, and K. Muñiz J. Org. Chem. 77 2012 1922 1930
    • (2012) J. Org. Chem. , vol.77 , pp. 1922-1930
    • Chávez, P.1    Kirsch, J.2    Streuff, J.3    Muñiz, K.4
  • 383
    • 79951827488 scopus 로고    scopus 로고
    • For a recent example of a gold-catalyzed Ritter reaction albeit one not involving aziridinium ions, see
    • For a recent example of a gold-catalyzed Ritter reaction albeit one not involving aziridinium ions, see: N. Ibrahim, A.S.K. Hashmi, and F. Rominger Adv. Synth. Catal. 353 2011 461 468
    • (2011) Adv. Synth. Catal. , vol.353 , pp. 461-468
    • Ibrahim, N.1    Hashmi, A.S.K.2    Rominger, F.3
  • 387
    • 77549085854 scopus 로고    scopus 로고
    • Despite its exotic appearance, compound 402 is readily available through the oxidation of N,N′-di-tert-butylurea
    • Despite its exotic appearance, compound 402 is readily available through the oxidation of N,N′-di-tert-butylurea: H. Du, B. Zhao, and Y. Shi Org. Synth. 86 2009 315 324
    • (2009) Org. Synth. , vol.86 , pp. 315-324
    • Du, H.1    Zhao, B.2    Shi, Y.3


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