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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 4
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Original Articles

Zirconium (IV) Chloride Catalyzed Ring Opening of Epoxides with Aromatic Amines

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Pages 727-734 | Received 22 Aug 2003, Published online: 16 Aug 2006

References

  • Corey , E. J. and Zhang , F. 1999 . re‐ and si‐Face‐selective nitroaldol reactions catalyzed by a rigid chiral quarternary ammonium salt: a highly stereoselective synthesis of the HIV protease inhibitor amprenavir (vertex 478) . Angew. Chem. Int. Ed. , 38 : 1931
  • Rogers , G. A. , Parson , S. M. , Anderson , D. C. , Nilsson , L. M. , Bahr , B. A. , Kornreich , W. D. , Kaufman , R. , Jacobson , R. S. and Kirtman , B. 1989 . Synthesis, in vitro acetylcholine‐storage‐blocking activities, and biological properties of derivatives and anlogues of trans‐2‐(4‐phenyl piperidino) cyclohexanol (vesamicol) . J. Med. Chem. , 32 : 1217 [PUBMED] [INFOTRIEVE]
  • Chng , B. L. and Ganesan , A. 1997 . Solution‐phase synthesis of a β‐amino alcohol combinatorial library . Bioorg. Med. Chem. Lett. , 7 : 1511 [CROSSREF]
  • Heiba , E. I. and Dessau , R. M. 1971 . Oxidation by metal salts VII syntheses based on the selective oxidation of free radicals, oxidation by metal salts VII the decomposition of ceric carboxylates in the presence of olefins and aromatic hydrocarbons . J. Am. Chem. Soc. , 93 : 524 – 995 .
  • 1972 . Oxidation by metal salts IX formation of cyclic ketones . Ibid. , 94 : 2888
  • Kurt , M. E. , Baru , V. and Ngugen , P. N. 1984 . Aromatic acetylation promoted by manganese (III) and cerium (IV) salts . J. Org. Chem. , 49 : 1603
  • Baciocchi , E. , Aira , D. D. and Ruzziconi , R. 1986 . Dimethyl arylmalonates from cerium (IV) ammonium nitrate promoted reactions of dimethyl malonate with aromatic compounds in methanol . Tetrahedron Lett. , 27 : 2763 [CROSSREF]
  • Baciocchi , E. and Ruzziconi , R. 1986 . 1,2‐ and 1,4‐addition in the reactions of carbonyl compounds with 1,3‐butadien induced by cerium (IV) ammonium nitrate . J. Org. Chem. , 51 : 1645
  • Forth , W. , Henschler , D. and Rummel , W. 1988 . Pharmakologie und Toxikologie Edited by: Forth , W. , Henschler , D. and Rummel , W. Wissenschaftsverlag Manheim .
  • Wnetton , A. and Neu , H. C. 1982 . The Aminoglyzosides Edited by: Wnetton , A. and Neu , H. C. New York : Marcel Dekker .
  • Horii , S. , Fukase , H. , Matsuo , T. , Kameda , Y. , Asano , N. and Matsui , K. 1986 . Synthesis and α‐D‐glucosidase inhibitory activity of n‐substituted valiolamine derivatives as potential oral antidiabetic agents . J. Med. Chem. , 29 : 1038 [PUBMED] [INFOTRIEVE]
  • Deyrup , J. A. and Moyer , C. L. 1969 . 1,2,3‐Oxathiazolidines‐a new heterocyclic system . J. Org. Chem. , 34 : 175
  • Crooks , P. A. and Szyndler , R. 1973 . Synthesis of β‐amino alcohols via spiro‐oxirane intermediates . Chem. Ind. (London) , : 1111
  • Auge , J. and Leroy , F. 1996 . Lithium trifluromethanesulfonate catalyzed aminolysis of oxiranes . Tetrahedron Lett. , 37 : 7715 (LiOTf) [CROSSREF]
  • Chini , M. , Crotti , P. , Favero , L. , Macchia , F. and Pineschi , M. 1994 . Lanthanide (III) trifluromethanesulfonate catalyzed extraordinarily effective new catalysts for the aminolysis 1,2‐epoxides . Tetrahedron Lett. , 35 : 433 [La(OTf)3] [CROSSREF]
  • Meguro , M. , Asao , N. and Yamamoto , Y. 1994 . Ytterbium triflate and high pressure‐mediated ring opening of epoxides with amines . J. Chem. Soc., Perkin Trans. 1 , : 2597 [Yb(OTf)3] [CROSSREF]
  • Fujiwara , M. , Imada , M. , Baba , A. and Matsuda , H. 1989 . Tetraphenyl stibonium as a regio‐ and chemoselective catalyst in the reaction of oxiranes with amines . Tetrahedron Lett. , 30 : 739 [Ph4SbOtf] [CROSSREF]
  • Chandrasekhar , S. , Ramachandar , T. and Jaya Prakash , S. 2000 . TaCl5 catalyzed cleavage of epoxides with aromatic amines . Synthesis , : 1817 [CROSSREF]
  • Sekar , G. and Singh , V. K. 1999 . An efficient method for cleavage of epoxides with aromatic amines . J. Org. Chem. , 64 : 287 [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Firouzabadi , H. , Iranpoor , N. and Karimi , B. 1999 . Zirconium tetrachloride (ZrCl4) catalyzed highly chemoselective and efficient transthioacetalization of acetals . Synlett , 3 : 319
  • Patney , H. K. and Margan , S. 1996 . Zirconium (IV) chloride silica catalyzed thioacetalization of carbonyl compounds . Tetrahedron Lett. , 37 : 4621 [CROSSREF]
  • Firouzabadi , H. , Iranpoor , N. and Karimi , B. 1999 . Zirconium (IV) tetrachloride catalyzed highly chemoselective and efficient acetalization of carbonyl compounds . Synlett , 3 : 321
  • Udry , K. B. , Rajaraman , S. and Soundararajan , N. 2002 . A practical synthesis of chloromethylester from acid chlorides and trioxanes or paraformaldehyde promoted by zirconium tetrachloride . Tetrahedron Lett. , 43 : 6317 [CROSSREF]

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