Ruthenium(III) Chloride–Catalyzed Ring Opening of Epoxides with Aromatic Amines

References

• Corey , E. J. and Zhang , F. 1999 . Re‐and si‐face‐selective nitroaldol reactions catalyzed by a rigid chiral quarternary ammonium salt . Angew. Chem., Int. Ed. Engl. , 38 : 1931
   PubMed Web of Science ®Google Scholar
• Chang , H. T. and Sharpless , K. B. 1996 . Catalytic asymmetric aminohydroxylation of olefins . Angew. Chem. Int. Ed. Engl. , 35 : 451
   Web of Science ®Google Scholar
• Ager , D. J. , Prakash , I. and Shaad , D. R. 1996 . 1,2‐Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis . Chem. Rev. , 96 : 835
   PubMed Web of Science ®Google Scholar
• Rogers , G. A. , Parson , S. M. , Anderson , D. C. , Nilson , L. M. , Bahr , B. A. , Kornreich , W. D. , Kaufman , R. , Jacobs , R. S. and Kirtman , B. 1989 . Synthesis, in vitro acetylcholine‐storage‐blocking activities, and biological properties of derivatives and analogs of trans‐2‐(4‐phenylpiperidino)cyclohexanol (vesamicol) . J. Med. Chem. , 32 : 1217
   PubMed Web of Science ®Google Scholar
• Cheng , B. L. and Ganesan , A. 1997 . A solution‐phase synthesis of a β‐amino alcohol combinatorial library . Bioorg. Med. Chem. Lett. , 7 : 1511
   Web of Science ®Google Scholar
• Ghosh , A. K. and Wang , Y. 1999 . Total synthesis of (+)‐polyoxin J . J. Org. Chem. , 64 : 2789
   PubMed Web of Science ®Google Scholar
• Yamaguchi , T. , Harada , N. , Ozaki , K. and Hashiyama , T. 1998 . Synthesis of taxoids 3. A novel and efficient method for preparation of taxoids by employing cis‐glycidic acid . Tetrahedron Lett. , 39 : 5575
   Web of Science ®Google Scholar
• Hodgson , D. M. , Gibbs , A. R. and Lee , G. P. 1996 . Enantioselective desymmetrisation of achiral epoxides . Tetrahedron , 52 : 14361
   Web of Science ®Google Scholar
• Hanson , R. M. 1991 . The synthetic methodology of nonracemic glycidol and related 2,3‐epoxy alcohols . Chem. Rev. , 91 : 437
   Web of Science ®Google Scholar
• Chini , M. , Croti , M. and Machia , F. 1991 . J. Org. Chem. , 66 : 5939
   Web of Science ®Google Scholar
• 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
   Web of Science ®Google Scholar
• Sekar , G. and Singh , V. K. 1999 . An efficient method for cleavage of epoxides with aromatic amines . J. Org. Chem. , 64 : 287
   PubMed Web of Science ®Google Scholar
• Chadrasekhar , S. , Ramchandar , T. and Prakash , J. S. 2000 . TaCl5‐catalyzed cleavage of epoxides with aromatic amines . Synthesis , 22 : 1818
   Google Scholar
• Chakraborti , A. K. 2003 . Kondaskar, A. ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines . Tetrahedron Lett. , 44 : 8315
   Web of Science ®Google Scholar
• Swamy , N. R. , Goud , T. V. , Reddy , S. M. , Krishnaiah , P. and Vekateswarlu , Y. 2004 . Zirconium(IV) chloride–catalyzed ring opening of epoxides with aromatic amines . Synth. Commun. , 34 : 727
   Web of Science ®Google Scholar
• Kissel , C. L. and Rickborn , B. 1972 . Base‐induced rearrangement of epoxides. IV. Reaction of cyclohexene oxide with various lithium alkylamides . J. Org. Chem. , 37 : 2060
   Web of Science ®Google Scholar
• Overman , L. E. and Flippin , L. A. 1981 . Facile aminolysis of epoxides with diethylaluminium amides . Tetrahedron Lett. , 22 : 195
   Web of Science ®Google Scholar
• Chini , M. , Crotti , P. and Machia , F. 1990 . Metal salts as new catalysts for mild and efficient aminolysis of oxiranes . Tetrahedron Lett. , 31 : 4661
   Web of Science ®Google Scholar
• Kotsuki , H. , Hayashida , K. , Shimanouchi , T. and Nishizawa , H. 1996 . High‐pressure organic chemistry. 19. High‐pressure‐promoted, silica gel‐catalyzed reaction of epoxides with nitrogen heterocycles . J. Org. Chem. , 61 : 984
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. , Basak , A. K. and Narsaiah , A. V. 2003 . [Bmin]BF4 ionic liquid: A novel reaction medium for the synthesis of β‐amino alcohols . Tetrahedron Lett. , 44 : 1047
   Web of Science ®Google Scholar
• Mojtahedi , M. M. , Saidi , M. R. and Bolortchian , M. 1999 . J. Chem. Res. , : 128
   Web of Science ®Google Scholar
• De , S. K. 2004 . Ruthenium(III) chloride–catalyzed acylation of alcohols, phenols, thiols, and amines . Tetrahedron Lett. , 45 : 2919
   Web of Science ®Google Scholar
• De , S. K. and Gibbs , R. A. 2004 . Ruthenium(III) chloride–catalyzed chemoselective synthesis of acetal from aldehydes . Tetrahedron Lett. , 45 : 8141
   Web of Science ®Google Scholar
• De , S. K. 2004 . RuCl3‐catalyzed facile conversion of arylalkyl ketoximes to amides . Synth. Comm. , 34 : 3431
   Web of Science ®Google Scholar