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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 14
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Original Articles

Synthesis of New and Novel N-Protected 1-Aminoalkyl-2-naphthol Derivatives

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Pages 2560-2574 | Received 29 Aug 2008, Published online: 16 Jun 2009

REFERENCES

  • (a) Seebach , D. ; Matthews , J. L. β-Peptides: A surprise at every turn . J. Chem. Soc., Chem. Commun. 1997 , 2015 – 2022 ; (b) Wang , Y.-F. ; Izawa , T. ; Kobayashi , S. ; Ohno , M. Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction . J. Am. Chem. Soc. 1982 , 104 , 6465 – 6466 ; (c) Knapp , S. Synthesis of complex nucleoside antibiotics . Chem. Rev. 1995 , 95 , 1859 – 1876 ; (d) Juaristi, E. In Enantioselective Synthesis of β-Amino Acids ; John Wiley & Sons: New York, 1997.
  • (a) Dingermann , T. ; Steinhilber , D. ; Folkers , G. In Molecular Biology in Medicinal Chemistry ; Wiley-VCH, Weinheim, Germany , 2004 ; (b) Shen, A. Y.; Tsai, C. T.; Chen, C. L. Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols. Eur. J. Med. Chem. 1999, 34, 877–882.
  • (a) Welch , W. M. ; Kraska , A. R. ; Sarges , R. ; Koe , B. K. Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins . J. Med. Chem. 1984 , 27 , 1508 – 1515 ; (b) Corey , E. J. ; Gant , T. G. A catalytic enantioselective synthetic route to the important antidepressant sertraline . Tetrahedron Lett. 1994 , 35 , 5373 – 5376 ; (c) Chen , C. ; Reamer , R. A. Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine . Org. Lett. 1999 , 1 , 293 – 294 ; (d) Davies , H. M. L. ; Stafford , D. G. ; Hansen , T. Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates: A formal asymmetric synthesis of (+)-sertraline . Org. Lett. 1999 , 1 , 233 – 236 .
  • For representative examples, see (a) Enders , D. ; Muller , S. F. ; Raabe , G. Enantioselective synthesis of β-amino sulfones by aza-Michael addition to alkenyl sulfones . Angew. Chem., Int. Ed. 1999 , 38 , 195 – 197 ; (b) Evans , D. A. ; Wu , L. D. ; Wiener , J. M. ; Johnson , J. S. ; Ripin , D. H. B. ; Tedrow , J. S. A general method for the synthesis of enantiomerically pure β-substituted, β-amino acids through α-substituted succinic acid derivatives . J. Org. Chem. 1999 , 64 , 6411 – 6417 ; (c) Kochi , T. ; Tang , T. P. ; Ellman , J. A. Asymmetric synthesis of syn- and anti-1,3-amino alcohols . J. Am. Chem. Soc. 2002 , 124 , 6518 – 6519 ; (d) Murai , T. ; Sano , H. ; Kawai , H. ; Aso , H. ; Shibahara , F. N-Thioacyl 1,3-amino alcohols: Synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5,6-dihydro-4H-1,3-oxazines and 1,3-amino alcohols . J. Org. Chem. 2005 , 70 , 8148 – 8153 ; (e) Keck , G. E. ; Truong , A. P. Directed reduction of β-amino ketones to syn or anti-1,3-amino alcohol derivatives . Org. Lett. 2002 , 4 , 3131 – 3134 ; (f) Ohno , H. ; Hamaguchi , H. ; Tanaka , T. Umpolung of chiral 2-Ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0) . Org. Lett. 2000 , 2 , 2161 – 2163 .
  • Green , W. ; Wats , M. P. G. Protecting Groups in Organic Synthesis; , 2nd ed.; John Wiley and Sons : New York , 1999.
  • (a) Chakraborti , A. K. ; Gulhane , R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines . Chem. Commun. 2003 , 1896 – 1897 ; (b) Chakraborti, A. K.; Gulhane, R. Indian Patent 266/DEL/2003, March 10, 2003; (c) Shaterian, H. R.; Shahrekipoor, F.; Ghashang, M. Silica-supported perchloric acid (HClO4–SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions. J. Mol. Catal. A: Chem. 2007, 272, 142–151; (d) Kamble, V. T.; Jamode, V. S.; Joshi, N. S.; Biradara, A. V.; Deshmukh, R. Y. An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2). Tetrahedron Lett. 2006, 47, 5573–5576; (e) Mukherjee, C.; Misra, A. K. Glycosylation and pyranose-furanose isomerization of carbohydrates using HClO4-SiO2: Synthesis of oligosaccharides containing galactofuranose. Synthesis 2007, 683–692; (f) Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Silica-supported perchloric acid (HClO4-SiO2): An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols. Tetrahedron 2008, 64, 1263–1269.

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