o-Benzenedisulfonimide as a Recyclable Homogeneous Organocatalyst for an Efficient and Facile Synthesis of 4-Amidotetrahydropyran Derivatives Through Prins–Ritter Reaction

REFERENCES

• (a) Barbero , M. ; Cadamuro , S. ; Dughera , S. ; Venturello , P. o-Benzenedisulfonimide: A novel and reusable catalyst for acid-catalyzed organic reactions . Synlett 2007 , 2209 – 2212 ; (b) Barbero , M. ; Cadamuro , S. ; Dughera , S. ; Venturello , P. o-Benzenedisulfonimide as reusable Brønsted acid catalyst for acid-catalyzed organic reactions . Synthesis 2008 , 1379 – 1388 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Barbero , M. ; Cadamuro , S. ; Deagostino , A. ; Dughera , S. ; Larini , P. ; Occhiato , G. ; Prandi , C. ; Tabasso , S. ; Venturello , P. ; Vulcano , R. o-Benzenedisulfonimide as a powerful and recyclable organocatalyst for the Nazarov reaction . Synthesis 2009 , 2260 – 2266 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• (a) Michelet , V. ; Genet , J.-P. An overview of synthetic and biological studies of ambruticin and analogues . Curr. Org. Chem. 2005 , 9 , 405 – 418 ; (b) 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 ; (c) Suhara , Y. ; Yamaguchi , Y. ; Collins , B. ; Schnaar , R. L. ; Yanagishita , M. ; Hildreth , J. E. K. ; Shimada , I. ; Ichikawa , Y. Oligomers of glycamino acid . Bioorg. Med. Chem. 2002 , 10 , 1999 – 2013 (d) 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 ; (e) 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-Neu5Acα2Me) . Tetrahedron Lett. 1995 , 36 , 5405 – 5408 ; (f) Sabesan , S. ; Neira , S. ; Wasserman , Z. Structural and functional-group tuning in the design of neuraminidase inhibitors . Carbohydr. Res. 1995 , 267 , 239 – 261 ; (g) Michelet , V. ; Genet , J. P. Curr. Org. Chem. 2005 , 9 , 405 (h) Snider , B. B. ; Hawryluk , N. A. Synthesis of (–)-dysiherbaine . Org. Lett. 2000 , 2 , 635 – 638 .
   Web of Science ®Google Scholar
• Sakata , H. ; Yasukawa , H. Jpn. Kokai Tokkyo Koho JP 2003121964 A , 2003 .
   Google Scholar
• (a) Yadav , J. S. ; Reddy , B. V. S. ; Kumar , G. G. K. S. N. ; Reddy , M. G. CeCl3 · 7H2O/AcCl-catalyzed Prins–Ritter reaction sequence: A novel synthesis of 4-amido tetrahydropyran derivatives. Tetrahedron Lett. 2007, 48, 4903–4906; (b) Reddy , U. C. ; Raju , B. R. ; Kumar , E. K. P. ; Saikia , A. K. Stereoselective one-pot, three-component synthesis of 4-amido tetrahydropyran. J. Org. Chem. 2008, 73, 1628–1630; (c) 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; (d) 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; (e) 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; (f) 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; (g) 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.
   Web of Science ®Google Scholar
• (a) 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 ; (b) 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 ; (c) 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 ; (d) 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 .
   Web of Science ®Google Scholar
• Castaldi , M. P. ; Troast , D. M. ; Porco , J. A. Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations . Org. Lett. 2009 , 11 , 3362 – 3365 .
   PubMed Web of Science ®Google Scholar
• (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 ; (b) Ramesh , J. ; Rychnovsky , S. D. Oxonia–Cope rearrangement and side-chain Exchange in the Prins cyclization . Org. Lett. 2006 , 8 , 2175 – 2178 ; (c) 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar