메뉴 건너뛰기




Volumn 44, Issue 17, 2014, Pages 2545-2554

O -benzenedisulfonimide as a recyclable homogeneous organocatalyst for an efficient and facile synthesis of 4-amidotetrahydropyran derivatives through prins-ritter reaction

Author keywords

4 Amidotetrahydropyrans; Br nsted acid; Hosomi Sakurai allylation; Prins Ritter amidation; recyclable catalyst; spiro tetrahydropyrans

Indexed keywords

2 BENZENEDISULFONIMIDE; 4 AMIDOTETRAHYDROPYRAN DERIVATIVE; ALDEHYDE; ALLYLTRIMETHYLSILANE; CARBON; NITRILE; SULFIDE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84904398680     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2014.909488     Document Type: Article
Times cited : (14)

References (33)
  • 1
    • 34548732384 scopus 로고    scopus 로고
    • O-benzenedisulfonimide: A novel and reusable catalyst for acid-catalyzed organic reactions
    • DOI 10.1055/s-2007-985559
    • Barbero, M.;, Cadamuro, S.;, Dughera, S.;, Venturello, P. o -Benzenedisulfonimide: A novel and reusable catalyst for acid-catalyzed organic reactions. Synlett 2007, 2209-2212 (Pubitemid 47436187)
    • (2007) Synlett , Issue.14 , pp. 2209-2212
    • Barbero, M.1    Cadamuro, S.2    Dughera, S.3    Venturello, P.4
  • 2
    • 44049101290 scopus 로고    scopus 로고
    • O-benzenedisulfonimide as reusable brønsted acid catalyst for acid-catalyzed organic reactions
    • DOI 10.1055/s-2008-1072564, Z01308SS
    • Barbero, M.;, Cadamuro, S.;, Dughera, S.;, Venturello, P. o -Benzenedisulfonimide as reusable Brønsted acid catalyst for acid-catalyzed organic reactions. Synthesis 2008, 1379-1388. (Pubitemid 351709854)
    • (2008) Synthesis , Issue.9 , pp. 1379-1388
    • Barbero, M.1    Cadamuro, S.2    Dughera, S.3    Venturello, P.4
  • 3
    • 58649091794 scopus 로고    scopus 로고
    • O -Benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: Advantages and limitations
    • Barbero, M.;, Cadamuro, S.;, Dughera, S.;, Venturello, P. o -Benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: Advantages and limitations. Synthesis 2008, 3625-3632.
    • (2008) Synthesis , pp. 3625-3632
    • Barbero, M.1    Cadamuro, S.2    Dughera, S.3    Venturello, P.4
  • 4
    • 73949085212 scopus 로고    scopus 로고
    • O -Benzenedisulfonimide as a reusable Brønsted acid catalyst for Hosomi-Sakurai reactions
    • Barbero, M.;, Bazzi, S.;, Cadamuro, S.;, Dughera, S.;, Piccinini, C. o -Benzenedisulfonimide as a reusable Brønsted acid catalyst for Hosomi-Sakurai reactions. Synthesis 2010, 315-319.
    • (2010) Synthesis , pp. 315-319
    • Barbero, M.1    Bazzi, S.2    Cadamuro, S.3    Dughera, S.4    Piccinini, C.5
  • 5
    • 58649097281 scopus 로고    scopus 로고
    • O -Benzenedisulfonimide as a reusable Brønsted acid catalyst for Ritter-type reactions
    • Barbero, M.;, Bazzi, S.;, Cadamuro, S.;, Dughera, S. o -Benzenedisulfonimide as a reusable Brønsted acid catalyst for Ritter-type reactions. Eur. J. Org. Chem. 2009, 430-436.
    • (2009) Eur. J. Org. Chem. , pp. 430-436
    • Barbero, M.1    Bazzi, S.2    Cadamuro, S.3    Dughera, S.4
  • 7
    • 68949128663 scopus 로고    scopus 로고
    • Synthetic and mechanistic aspects of acid-catalyzed disproportionation of dialkyl diarylmethyl ethers: A combined experimental and theoretical study
    • Barbero, M.;, Bazzi, S.;, Cadamuro, S.;, Dughera, S.;, Ghigo, G. Synthetic and mechanistic aspects of acid-catalyzed disproportionation of dialkyl diarylmethyl ethers: A combined experimental and theoretical study. Eur. J. Org. Chem. 2009, 4346-4351.
    • (2009) Eur. J. Org. Chem. , pp. 4346-4351
    • Barbero, M.1    Bazzi, S.2    Cadamuro, S.3    Dughera, S.4    Ghigo, G.5
  • 8
    • 84860783753 scopus 로고    scopus 로고
    • O-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot, three-component Strecker reaction: Synthetic and mechanistic aspects
    • Barbero, M.;, Cadamuro, S.;, Dughera, S.;, Ghigo, G. o- Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot, three-component Strecker reaction: Synthetic and mechanistic aspects. Org. Biomol. Chem. 2012, 10, 4058-4068.
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 4058-4068
    • Barbero, M.1    Cadamuro, S.2    Dughera, S.3    Ghigo, G.4
  • 9
    • 14844297343 scopus 로고    scopus 로고
    • An overview of synthetic and biological studies of ambruticin and analogues
    • Michelet, V.;, Genet, J.-P. An overview of synthetic and biological studies of ambruticin and analogues. Curr. Org. Chem. 2005, 9, 405-418 (Pubitemid 40347617)
    • (2005) Current Organic Chemistry , vol.9 , Issue.5 , pp. 405-418
    • Michelet, V.1    Genet, J.-P.2
  • 10
    • 84904396985 scopus 로고    scopus 로고
    • Hoefle, G.;, Steinmetz, H.;, Gerth, K.;, Reichenbach, H. Ambruticins VS: New members of the antifungal ambruticin family from Sorangium cellulosum. Liebigs Ann. Chem. 1991, 941-945
    • Hoefle, G.1    Steinmetz, H.2    Gerth, K.3    Reichenbach, H.4
  • 12
    • 0027972107 scopus 로고
    • Synthesis of a sialic acid analog with the acetamido group at C-4
    • DOI 10.1016/S0957-4166(00)86296-5
    • Dondoni, A.;, Boscarato, A.;, Marra, A. Synthesis of a sialic acid analog with the acetamido group at C-4. Tetrahedron: Asymmetry 1994, 5, 2209-2212 (Pubitemid 24355407)
    • (1994) Tetrahedron Asymmetry , vol.5 , Issue.11 , pp. 2209-2212
    • Dondoni, A.1    Boscarato, A.2    Marra, A.3
  • 13
    • 0029056482 scopus 로고
    • Synthesis of methyl 5-acetamido-3,4,5-trideoxy-4-guanidinyl-D-glycero-D- galacto-2-nonulopyranosidonic acid (4-deoxy-4-guanidino-Neu5Ac α 2Me)
    • Ciccotosto, S.;, von Itzstein, M. Synthesis of methyl 5-acetamido-3,4,5-trideoxy-4-guanidinyl-D-glycero-D-galacto-2- nonulopyranosidonic acid (4-deoxy-4-guanidino-Neu5Ac α 2Me). Tetrahedron Lett. 1995, 36, 5405-5408
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5405-5408
    • Ciccotosto, S.1    Von Itzstein, M.2
  • 14
    • 0028861406 scopus 로고
    • Structural and functional-group tuning in the design of neuraminidase inhibitors
    • Sabesan, S.;, Neira, S.;, Wasserman, Z. Structural and functional-group tuning in the design of neuraminidase inhibitors. Carbohydr. Res. 1995, 267, 239-261
    • (1995) Carbohydr. Res. , vol.267 , pp. 239-261
    • Sabesan, S.1    Neira, S.2    Wasserman, Z.3
  • 16
    • 0034624586 scopus 로고    scopus 로고
    • Synthesis of (-)-dysiherbaine
    • Snider, B. B.;, Hawryluk, N. A. Synthesis of (-)-dysiherbaine. Org. Lett. 2000, 2, 635-638.
    • (2000) Org. Lett. , vol.2 , pp. 635-638
    • Snider, B.B.1    Hawryluk, N.A.2
  • 17
    • 84904396989 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 2003121964 A.
    • Sakata, H.;, Yasukawa, H. Jpn. Kokai Tokkyo Koho JP 2003121964 A, 2003.
    • (2003)
    • Sakata, H.1    Yasukawa, H.2
  • 18
    • 34250004903 scopus 로고    scopus 로고
    • 2O/AcCl-catalyzed Prins-Ritter reaction sequence: A novel synthesis of 4-amido tetrahydropyran derivatives
    • DOI 10.1016/j.tetlet.2007.05.056, PII S0040403907009215
    • 2O/AcCl-catalyzed Prins-Ritter reaction sequence: A novel synthesis of 4-amido tetrahydropyran derivatives. Tetrahedron Lett. 2007, 48, 4903-4906 (Pubitemid 46891547)
    • (2007) Tetrahedron Letters , vol.48 , Issue.28 , pp. 4903-4906
    • Yadav, J.S.1    Reddy, B.V.S.2    Kumar, G.G.K.S.N.3    Reddy, G.M.4
  • 20
    • 39149143984 scopus 로고    scopus 로고
    • Three-component, one-pot diastereoselective synthesis of 4-amidotetrahydropyrans via the Prins-Ritter reaction sequence
    • Yadav, J. S.;, Reddy, B. V. S.;, Aravind, S.;, Kumar, G. G. K. S. N.;, Madhavi, C.;, Kunwar, A. C. Three-component, one-pot diastereoselective synthesis of 4-amidotetrahydropyrans via the Prins-Ritter reaction sequence. Tetrahedron 2008, 64, 3025-3031
    • (2008) Tetrahedron , vol.64 , pp. 3025-3031
    • Yadav, J.S.1    Reddy, B.V.S.2    Aravind, S.3    Kumar, G.G.K.S.N.4    Madhavi, C.5    Kunwar, A.C.6
  • 21
    • 49649119624 scopus 로고    scopus 로고
    • A Sakurai-Prins-Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate
    • Sabitha, G.;, Bhikshapathi, M.;, Nayak, S.;, Yadav, J. S.;, Ravi, R.;, Kunwar, A. C. A Sakurai-Prins-Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate. Tetrahedron Lett. 2008, 49, 5727-5731
    • (2008) Tetrahedron Lett. , vol.49 , pp. 5727-5731
    • Sabitha, G.1    Bhikshapathi, M.2    Nayak, S.3    Yadav, J.S.4    Ravi, R.5    Kunwar, A.C.6
  • 22
    • 78650400877 scopus 로고    scopus 로고
    • Molecular iodine-catalyzed, one-pot, diastereoselective synthesis of 4-amidotetrahydropyran
    • Sabitha, G.;, Bhikshapathi, M.;, Nayak, S.;, Yadav, J. S. Molecular iodine-catalyzed, one-pot, diastereoselective synthesis of 4- amidotetrahydropyran. Synth. Commun. 2010, 41, 8-15
    • (2010) Synth. Commun. , vol.41 , pp. 8-15
    • Sabitha, G.1    Bhikshapathi, M.2    Nayak, S.3    Yadav, J.S.4
  • 23
    • 80051693407 scopus 로고    scopus 로고
    • Iodine/AcCl-catalysed Prins/Ritter reaction: Synthesis of 4-amido tetrahydropyran
    • Srinavasan, P.;, Perumal, P. T.;, Raja, S. Iodine/AcCl-catalysed Prins/Ritter reaction: Synthesis of 4-amido tetrahydropyran. Indian J. Chem. 2011, 50B, 1083-1091
    • (2011) Indian J. Chem. , vol.50 B , pp. 1083-1091
    • Srinavasan, P.1    Perumal, P.T.2    Raja, S.3
  • 24
    • 84873402882 scopus 로고    scopus 로고
    • Stereoselective synthesis of anti -1,3-amino alcohols via reductive opening of 4-amidotetrahydropyrans derived from the Prins/Ritter sequence
    • Yadav, J. S.;, Reddy, Y. J. S.;, Reddy, P. N. A.;, Reddy, B. V. S. Stereoselective synthesis of anti -1,3-amino alcohols via reductive opening of 4-amidotetrahydropyrans derived from the Prins/Ritter sequence. Org. Lett. 2013, 15, 546-549.
    • (2013) Org. Lett. , vol.15 , pp. 546-549
    • Yadav, J.S.1    Reddy, Y.J.S.2    Reddy, P.N.A.3    Reddy, B.V.S.4
  • 25
    • 14644430985 scopus 로고    scopus 로고
    • A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: Synthesis of (+)-prelactones B, C and V
    • DOI 10.1016/j.tetlet.2005.01.121
    • Yadav, J. S.;, Reddy, M. S.;, Prasad, A. R. A convergent route to β -hydroxy δ -lactones through Prins cyclisation as the key step: Synthesis of (+)-prelactones B, C, and V. Tetrahedron Lett. 2005, 46, 2133-2136 (Pubitemid 40311244)
    • (2005) Tetrahedron Letters , vol.46 , Issue.12 , pp. 2133-2136
    • Yadav, J.S.1    Reddy, M.S.2    Prasad, A.R.3
  • 26
    • 33646780245 scopus 로고    scopus 로고
    • Stereoselective synthesis of anti-1,3-diol units via Prins cyclisation: Application to the synthesis of (-)-sedamine
    • DOI 10.1016/j.tetlet.2006.04.102, PII S0040403906008264
    • Yadav, J. S.;, Reddy, M. S.;, Rao, P. P.;, Prasad, A. R. Stereoselective synthesis of anti-1,3-diol units via Prins cyclisation: Application to the synthesis of (-)-sedamine. Tetrahedron Lett. 2006, 47, 4397-4401 (Pubitemid 43767583)
    • (2006) Tetrahedron Letters , vol.47 , Issue.26 , pp. 4397-4401
    • Yadav, J.S.1    Reddy, M.S.2    Rao, P.P.3    Prasad, A.R.4
  • 27
    • 48149110812 scopus 로고    scopus 로고
    • Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
    • Yadav, J. S.;, Rao, P. P.;, Reddy, M. S.;, Prasad, A. R. Stereoselective synthesis of basiliskamides A and B via Prins cyclisation. Tetrahedron Lett. 2008, 49, 5427-5430
    • (2008) Tetrahedron Lett. , vol.49 , pp. 5427-5430
    • Yadav, J.S.1    Rao, P.P.2    Reddy, M.S.3    Prasad, A.R.4
  • 28
    • 54849355200 scopus 로고    scopus 로고
    • The stereoselective total synthesis of xestodecalactone C and epi-sporostatin via the Prins cyclisation
    • Yadav, J. S.;, Thrimurtulu, N.;, Gayathri, K. U.;, Reddy, B. V. S.;, Prasad, A. R. The stereoselective total synthesis of xestodecalactone C and epi-sporostatin via the Prins cyclisation. Tetrahedron Lett. 2008, 49, 6617-6620.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 6617-6620
    • Yadav, J.S.1    Thrimurtulu, N.2    Gayathri, K.U.3    Reddy, B.V.S.4
  • 29
    • 68149144268 scopus 로고    scopus 로고
    • Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations
    • Castaldi, M. P.;, Troast, D. M.;, Porco, J. A. Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations. Org. Lett. 2009, 11, 3362-3365.
    • (2009) Org. Lett. , vol.11 , pp. 3362-3365
    • Castaldi, M.P.1    Troast, D.M.2    Porco, J.A.3
  • 30
    • 0037042279 scopus 로고    scopus 로고
    • Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking prins with cope and grob
    • DOI 10.1021/ja025902+
    • (a), Alder, R. W.;, Harvey, J. N.;, Oakley, M. T. Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations: Linking Prins with Cope and Grob. J. Am. Chem. Soc. 2002, 124, 4960-4961 (Pubitemid 34495880)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.18 , pp. 4960-4961
    • Alder, R.W.1    Harvey, J.N.2    Oakley, M.T.3
  • 31
    • 33744746980 scopus 로고    scopus 로고
    • Oxonia-Cope rearrangement and side-chain Exchange in the Prins cyclization
    • Ramesh, J.;, Rychnovsky, S. D. Oxonia-Cope rearrangement and side-chain Exchange in the Prins cyclization. Org. Lett. 2006, 8, 2175-2178
    • (2006) Org. Lett. , vol.8 , pp. 2175-2178
    • Ramesh, J.1    Rychnovsky, S.D.2
  • 32
    • 33744470881 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure 2,3,4,6-tetrasubstituted tetrahydropyrans by Prins-type cyclization of methyl ricinoleate and aldehydes
    • Biermann, U.;, Lutzen, A.;, Metzger, J. O. Synthesis of enantiomerically pure 2,3,4,6-tetrasubstituted tetrahydropyrans by Prins-type cyclization of methyl ricinoleate and aldehydes. Eur. J. Org. Chem. 2006, 2631-2637.
    • (2006) Eur. J. Org. Chem. , pp. 2631-2637
    • Biermann, U.1    Lutzen, A.2    Metzger, J.O.3
  • 33
    • 0031850093 scopus 로고    scopus 로고
    • New dry arenediazonium salts, stabilized to an exceptionally high degree by the anion of o -benzenedisulfonimide
    • Barbero, M.;, Crisma, M.;, Degani, I.;, Fochi, R.;, Perracino, P. New dry arenediazonium salts, stabilized to an exceptionally high degree by the anion of o -benzenedisulfonimide. Synthesis 1998, 1171-1175.
    • (1998) Synthesis , pp. 1171-1175
    • Barbero, M.1    Crisma, M.2    Degani, I.3    Fochi, R.4    Perracino, P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.