B₂O₃/Al₂O₃ as an Efficient and Recyclable Catalyst for the Synthesis of β-Amino Alcohols under Solvent-Free Conditions

REFERENCES

• (a) Corey , E. J. ; Zhang , F. Re- and Si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (vertex 478) . Angew. Chem., Int. Ed. 1999 , 38 , 1931 – 1934 ; (b) Johannes , C. W. ; Visser , M. S. ; Weatherhead , G. S. ; Hoveyda , A. H. Zr-catalyzed kinetic resolution of allylic ethers and Mo-catalyzed chromene formation in synthesis: Enantioselective total synthesis of the antihypertensive agent (S, R, R, R)-nebivolol . J. Am. Chem. Soc. 1998 , 120 , 8340 – 8347 ; (c) Chang , B. L. ; Ganesan , A. Solution-phase synthesis of a β-amino alcohol combinatorial library . Med. Chem. Lett. 1997 , 7 , 1511 – 1514 ; (d) Rogers , G. A. ; Parson , S. M. ; Anderson , D. S. ; Nilson , L. M. ; Bahr , B. A. ; Kornreich , W. D. ; Kaufman , R. ; Jacobs , R. S. ; Kirtman , B. Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol) . J. Med. Chem. 1989 , 32 , 1217 – 1230 .
   Google Scholar
• (a) O'Brien , P. Sharpless asymmetric aminohydroxylation: Scope, limitations, and use in synthesis . Angew. Chem., Int. Ed. 1999 , 38 , 326 – 329 ; (b) Li , G. ; Chang , H. T. ; Sharpless , K. B. Catalytic asymmetric aminohydroxylation (AA) of olefins . Angew. Chem, Int. Ed. 1996 , 35 , 451 – 454 .
   PubMed Web of Science ®Google Scholar
• Ager , D. J. ; Prakash , I. ; Schaad , D. R. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis . Chem. Rev. 1996 , 96 , 835 – 876 .
   PubMed Web of Science ®Google Scholar
• (a) Hodgson , D. M. ; Gibbs , A. R. ; Lee , G. P. Enantioselective desymmetrisation of achiral epoxides . Tetrahedron 1996 , 52 , 14361 – 14384 ; (b) Bergmeier , S. C. The synthesis of vicinal amino alcohols . Tetrahedron 2000 , 56 , 2561 – 2576 .
   Web of Science ®Google Scholar
• (a) Kissel , C. L. ; Rickborn , B. Base-induced rearrangement of epoxides, IV: Reaction of cyclohexene oxide with various lithium alkylamides . J. Org, Chem. 1972 , 37 , 2060 – 2063 ; (b) Carre , M. C. ; Houmounou , J. P. ; Caubere , P. A convenient preparation of β-amino alcohols from epoxides and halomagnesium alkylamides . Tetrahedron Lett. 1985 , 26 , 3107 – 3110 ; (c) Yamada , J. ; Yumoto , M. ; Yamamoto , Y. Aminolead compounds as a new reagent for regioselective ring opening of epoxides . Tetrahedron Lett. 1989 , 32 , 4255 – 4258 ; (d) Fiorenza , M. ; Ricci , A. ; Taddel , M. ; Tassi , D. Regiospecific conversion of oxiranes into primary alcohols via reaction with organotin derivatives . Synthesis 1983 , 640 .
   Web of Science ®Google Scholar
• (a) Rampalli , S. ; Chaudhari , S. S. ; Akamanchhi , K. G. Diisopropoxyaluminium trifluoroacetate: A new promoter for aminolysis of epoxides . Synthesis 2000 , 22 , 78 – 80 ; (b) Sagawa , S. ; Abe , H. ; Hase , Y. ; Inaba , T. Catalytic asymmetric aminolysis of 3,5,8-trioxabicyclo[5.1.0]octane providing an optically pure 2-amino-1,3,4-butanetriol equivalent . J. Org, Chem. 1999 , 64 , 4962 – 4965 .
   Google Scholar
• (a) Auge , J. ; Leroy , F. Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes. Tetrahedron Lett. 1996, 37, 7715–7716; (b) Fujiwara , M. ; Imada , M. ; Baba , A. ; Matsuda , H. Tetraphenylstibonium triflate as a regio- and chemoselective catalyst in the reaction of oxiranes with amines. Tetrahedron Lett. 1989, 30, 739–742; (c) Chini , M. ; Croti , P. ; Favero , L. ; Macchia , M. ; Pineschi , M. Lanthanide(III) trifluoromethanesulfonates as extraordinarily effective new catalysts for the aminolysis of 1,2-epoxides. Tetrahedron Lett. 1994, 35, 433–436; (d) Beaton , M. ; Gani , D. Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)-1,6-epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution. Tetrahedron Lett. 1998, 39, 8549–8552; (e) Placzek , A. T. ; Donelson , J. L. ; Trivedi , R. ; Richard A. ; Gibbs , R. A. ; De , S. K. Scandium triflate as an efficient and useful catalyst for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines under solvent-free conditions. Tetrahedron Lett. 2005, 46, 9029–9034; (f) Alam , M. ; Mujahid , V. R. ; Enugala , R. ; Adapa , S. R. Synthesis of β-amino alcohols by regioselective ring opening of epoxides with aromatic amines catalyzed by tin (II) chloride. Lett. Org. Chem. 2006, 3, 187–190.
   Web of Science ®Google Scholar
• (a) Chandrasekhar , S. ; Ramachandar , T. ; Prakash , J. S. TaCl5-Catalyzed cleavage of epoxides with aromatic amines . Synthesis 2000 , 1817 – 1818 ; (b) Chakraborti , A. K. ; Kondaskar , A. ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines . Tetrahedron Lett. 2003 , 44 , 8315 – 8319 ; (c) Swamy , N. R. ; Goud , T. V. ; Reddy , S. M. ; Krishnaiah , P. ; Venkateswarlu , Y. Zirconium(IV) chloride catalyzed ring opening of epoxides with aromatic amines . Synth. Commun. 2004 , 34 , 727 – 734 ; (d) Sabita , G. ; Reddy , G. S. ; Reddy , K. V. ; Yadav , J. S. Vanadium(III) chloride-catalyzed preparation of β-amino alcohols from epoxides . Synthesis 2003 , 2298 – 2300 ; (e) Pachon , L. D. ; Gamez , P. ; VanBrussel , J. J. ; Redijk , J. Zinc-catalyzed aminolysis of epoxides . Tetrahedron Lett. 2003 , 44 , 6025 – 6027 ; (f) Reddy , L. R. ; Reddy , M. A. ; Bhanumati , N. ; Rao , K. R. Cerium chloride-catalysed cleavage of epoxides with aromatic amines . Synthesis 2001 , 83 ; (g) McCluskey , A. ; Leitch , S. K. ; Garner , J. ; Caden , C. E. BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: One reagent, two paths . Tetrahedron Lett. 2005 , 46 , 8229 – 8232 .
   Google Scholar
• Kotsuki , H. ; Hayashida , K. ; Shimanouchi , T. ; Nishizawa , H. High-pressure organic chemistry, 19: High-pressure-promoted, silica gel–catalyzed reaction of epoxides with nitrogen heterocycles . J. Org. Chem. 1996 , 61 , 984 – 990 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. ; Basak , A. K. ; Narasaiah , A. V. [Bmim]BF4 ionic liquid: A novel reaction medium for the synthesis of β-amino alcohols . Tetrahedron Lett. 2003 , 44 , 1047 – 1050 .
   Web of Science ®Google Scholar
• Azizi , N. ; Saidi , M. R. Highly chemoselective addition of amines to epoxides in water . Org. Lett. 2005 , 7 , 3649 – 3651 .
   PubMed Web of Science ®Google Scholar
• Mojtahedi , M. M. ; Saidi , M. R. ; Bolrtchian , M. Microwave-assisted aminolysis of epoxides under solvent-free conditions catalyzed by montmorillonite clay . J. Chem. Res. ( S ) 1999 , 128 – 129 .
   Google Scholar
• (a) Harrak , Y. ; Pujol , M. D. Mild cleavage of aliphatic epoxides with substituted anilines on alumina . Tetrahedon Lett. 2002 , 43 , 819 – 822 ; (b) Chini , M. ; Crotti , P. ; Flippin , L. A. ; Macchia , F. Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes, 3: Aminolysis and azidolysis of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene . J. Org. Chem. 1991 , 56 , 7043 – 7048 ; (c) Desai , R. C. A convenient synthesis of the novel hypoglycemic agent SDZ PGU 693 . J. Org. Chem. 2001 , 66 , 4939 – 4940 ; (d) Chini , M. ; Crotti , P. ; Macchia , M. Metal salts as new catalysts for mild and efficient aminolysis of oxiranes . Tetrahedron Lett. 1990 , 31 , 4661 – 4664 ; (e) Schneider , C. ; Sreekanth , A. R. ; Mai , E. Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides . Angew. Chem., Int. Ed. 2004 , 43 , 5691 – 5694 ; (f) Rafiee , E. ; Tangesnijad , S. ; Habibi , M. H. ; Mirkhani , V. P. Dodecatungstocobaltate trihydrate (K5COW12O40 · 3H2O) as an efficient catalyst for aminolysis of epoxides . Synth. Commun. 2004 , 34 , 3673 – 3682 ; (g) Khosrpour , A. R. ; Khadaei , M. M. ; Ghozati , K. Bi(OTf)3- and Bi(TFA)3-catalyzed ring opening of epoxides with anilines under microwave irradiation . Chem. Lett. 2004 , 33 , 304 – 305 ; (h) Ollevier , T. ; Compin , G. L. Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions . Tetrahedron Lett. 2004 , 45 , 49 – 52 ; (i) Zhao , P. Q. ; Xu , L. W. ; Xia , C. G. Polystyrene-bound cinchona alkaloids: Application to enantioselective electrophilic fluorination of silyl enol ethers . Synlett 2004 , 856 – 860 ; (j) Chakraborti , A. ; Kondaskar , A. ; Rudrawar , S. Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines . Tetrahedron 2004 , 60 , 9085 ; (k) Wu , J. ; Xio , H. G. Tertiary amines as highly efficient catalysts in the ring-opening reactions of epoxides with amines or thiols in H2O: Expeditious approach to β-amino alcohols and β-aminothioethers . Green Chem. 2005 , 7 , 708 – 710 ; (l) Kamal , A. ; Ramu , R. ; Azhar , M. ; Khanna , G. B. Copper(II) tetrafluoroborate-catalyzed ring-opening of epoxides by amines . Tetrahedron Lett. 2005 , 46 , 2675 – 2677 ; (m) Peters , A. T. ; Sener , M. E. Disperse dyes derived from 4-phenylazo-1-naphthylamine and 4-phenylazo-5-hydroxy-1-naphthylamine . Dyes Pigments 1987 , 8 , 99 – 118 ; (n) Su , Z. Y. ; Mariano , P. S. ; Falvey , D. E. Dynamics of anilinium radical α-heterolytic fragmentation processes: Electrofugal group, substituent, and medium effects on desilylation, decarboxylation, and retro-aldol cleavage pathways . J. Am. Chem. Soc. 1998 , 120 , 10676 – 10686 ; (o) Reddy , Y. V. ; Saraswathy , M. ; Venkateswara , R. B. ; Shekharam , T. Polymer supported copper sulphate promoted aminolysis of epoxides with aromatic amines . Catal. Commun. 2006 , 7 , 466 – 471 .
   Google Scholar
• Robinson , M. W. C. ; Timms , D. A. ; Williams , S. M. ; Graham , A. E. A mild and efficient synthesis of β-amino alcohols from epoxides using a mesoporous aluminosilicate catalyst . Tetrahedron Lett. 2007 , 48 , 6249 – 6251 .
   Web of Science ®Google Scholar
• Satyarthi , J. K. ; Srinivas , L. S. D. ; Ratnasamy , P. Regio- and stereoselective synthesis of β-amino alcohols over titanosilicate molecular sieves . Appl. Catal. A: Gen. 2007 , 330 , 145 – 151 .
   Google Scholar
• Kabalka , G. W. ; Pagni , R. M. Organic reactions on alumina . Tetrahedron 1997 , 53 , 7999 – 8065 .
   Web of Science ®Google Scholar
• (a) McKillop , A. ; Young , D. W. Organic synthesis using supported reagents, part I. Synthesis 1979, 401–422; (b) McKillop , A. ; Young , D. W. Organic synthesis using supported reagents, part II. Synthesis 1979, 481–500; (c) Chakraborti , A. K. ; Rudrawar , S. ; Kondaskar , A. An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines. Org. Biomol. Chem. 2004, 2, 1277–1280.
   Google Scholar