Facile Synthesis of Aminoalcohols by Ring Opening of Epoxides Under Solvent Free Conditions

References

• Anger , D. J. , Prakash , I. and Schaad , D. R. 1996 . 1,2‐Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis . Chem. Rev. , 96 ( 2 ) : 835 – 875 .
   Google Scholar
• Iida , T. , Yamamoto , N. , Sasai , H. and Shibasaki , M. 1997 . New asymmetric reactions using a gallium complex: a highly enantioselective ring opening of epoxides with thiols catalyzed by a gallium·lithium·bis(binapthoxide) complex . J. Am. Chem. Soc. , 119 ( 20 ) : 4783 – 4784 .
   Google Scholar
• Wu , M. H. and Jacobsen , E. N.J. 1998 . Asymmetric ring opening of meso epoxides with thiols: enantiomeric enrichment using a bifunctional nucleophile . Org. Chem. , 63 ( 15 ) : 5252 – 5254 .
   Google Scholar
• Buono , G. 2001 . On the beneficial effect of ortho‐methoxy groups in the asymmetric ring opening of meso epoxides with silicon tetrachloride catalyzed by chiral ortho‐methoxyphenyldiazaphosphonamide Lewis bases . Angew. Chem. Int. Ed. , 40 ( 24 ) : 4536
   Google Scholar
• Adams , H. , Bell , R. , Cheung , Y.‐Y. , Jones , D. N. and Tomkinson , N. C.O. 1999 . The cleavage of meso‐epoxides with homochiral thiols: synthesis of (+)‐ and (−)‐trans‐1‐mercaptocyclohexan‐2‐ol . Tetrahedron: Asymmetry , 10 ( 21 ) : 4129 – 4142 .
   Google Scholar
• Wu , J. , Hou , X.‐L. , Dai , L.‐X. , Xia , L.‐J. and Tang , M.‐H. 1998 . Enantioselective ring opening of meso‐epoxides with thiols catalyzed by a chiral (salen) Ti(IV) complex . Tetrahedron: Asymmetry , 9 ( 19 ) : 3431 – 3436 .
   Google Scholar
• Rogers , G. A. , Parsons , Anderson , D. C. , Nilsson , 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 analogues of trans‐2‐(4‐phenylpeperidino)cyclohexanol (vesamicol) . J. Med. Chem. , 32 ( 6 ) : 1217 – 1230 .
   Google Scholar
• Mousseron , M. , Jullien , J. and Jolchine , Y. 1952 . Obtention et propriétés d'amines substitutées . Bull. Soc. Chim. Fr. , : 757 – 766 .
   Google Scholar
• Deyrup , J. A. and Moyer , C. L. 1969 . 1,2,3‐Oxathiazolidines. Heterocyclic system . J. Org. Chem. , 34 ( 1 ) : 175 – 179 .
   Web of Science ®Google Scholar
• Chini , M. , Crotti , C. and Macchia , F. 1990 . Metal salts as new catalysts for mild and efficient aminolysis of oxiranes . Tetrahedron Lett. , 31 ( 32 ) : 4661 – 4664 .
   Google Scholar
• Chini , M. , Crotti , P. and Macchia , F. 1991 . Regioalternatig selectivity in the metal salt catalyzed aminolysis of styrene oxide . J. Org. Chem. , 56 ( 20 ) : 5939 – 5942 .
   Google Scholar
• Ollevier , T. and Lavie‐Compin , G. 2002 . An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride . Tetrahedron Lett. , 43 ( 44 ) : 7891 – 7893 .
   Google Scholar
• Swamy , R. N. , Kondaji , G. and Nagaiah , K. 2002 . Bi3+ catalyzed regioselective ring opening of epoxides with aromatic amines . Synth. Commun. , 32 ( 15 ) : 2307 – 2312 .
   Google Scholar
• Chandrasekhar , S. , Ramachandar , S. and Prakash , J. S. 2000 . TaCl5 catalysed cleavage of epoxides with aromatic amines . Synthesis , : 1817 – 1818 .
   Google Scholar
• Fu , X. L. and Wu , S. H. 1997 . A regio and stereoselective synthesis of β‐amino alcohols . Synth. Commun. , 27 ( 10 ) : 1677 – 1683 .
   Web of Science ®Google Scholar
• Weghe , P. and Collin , J. 1995 . Ring opening reactions of epoxides catalyzed by samarium iodides . Tetrahedron Lett. , 36 ( 10 ) : 1649 – 1652 .
   Google Scholar
• Reddy , L. R. , Reddy , M. A. , Bhanumathi , N. and Rao , K. R. 2001 . Cerium chloride catalysed cleavage of epoxides with aromatic amines . Synthesis , : 831 – 832 .
   Google Scholar
• Chini , M. , Crotti , P. , Favero , L. , Macchia , F. and Pineschi , M. 1994 . Lanthanide(III) trifluoromethanesulfonates as extraordinarily effective new catalysts for the aminolysis of 1,2‐epoxides . Tetrahedron Lett. , 35 ( 3 ) : 433 – 436 .
   Google Scholar
• Sekar , G. and Singh , V. K. 1999 . An efficient method for cleavage of epoxides with aromatic amines . J. Org. Chem. , 64 ( 1 ) : 287 – 289 .
   Google Scholar
• Chandrasekhar , S. , Reddy , C. R. , Babu , B. N. and Chandrashekar , G. 2002 . Highly efficient cleavage of epoxides catalyzed by B(C6F5)3 . Tetrahedron Lett. , 43 ( 21 ) : 3801 – 3803 .
   Google Scholar
• Currini , M. , Epifano , F. , Marcotullio , M. C. and Rosati , O. 2001 . Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β‐amino alcohols from epoxides . Eur. J. Org. Chem. , : 4149 – 4152 .
   Google Scholar
• Das , U. , Crousse , B. , Kesavan , V. , Bonnet‐Delpon , D. and Bégué , J. P. 2000 . Facile ring opening of oxiranes with aromatic amines in fluoro alcohols . J. Org. Chem. , 65 ( 20 ) : 6749 – 6751 .
   PubMedGoogle Scholar
• Yadav , J. S. , Reddy , B. V.S. , Basak , A. K. and Narsaiah , A. V. 2003 . [Bmim]BF4 ionic liquid: a novel reaction medium for the synthesis of β‐amino alcohols . Tetrahedron Lett. , 44 ( 5 ) : 2721 – 1050 .
   Google Scholar
• Harrak , Y. and Pujol , M. D. 2002 . Mild cleavage of aliphatic epoxides with substituted anilines on alumina . Tetrahedron Lett. , 43 ( 5 ) : 819 – 822 .
   Google Scholar
• Lindström , B. , Olofsson , B. and Somfai , P. 1999 . Microwave‐assisted aminolysis of vinylepoxides . Tetrahedron Lett. , 40 ( 52 ) : 9273 – 9276 .
   Google Scholar
• Mojtahedi , M. M. , Saidi , M. R. and Bolourtchian , M. 1999 . Microwave‐assisted aminolysis of epoxides under solvent‐free conditions catalyzed by Montmorillonite clay . J. Chem. Res. (S) , : 128 – 129 .
   Google Scholar
• Santes , V. , Gómez , E. , Jiménez , G. , Santillan , R. , Gutiérrez , A. and Farfán , N. 2000 . Syntheses and study of new 2‐hydroxy‐5,6‐dihydro‐2H‐1,4‐oxazines by NMR and X‐ray crystallography . Synth. Commun. , 30 ( 15 ) : 2721 – 2734 .
   Web of Science ®Google Scholar
• Santes , V. , Gómez , E. , Santillan , R. and Farfán , N. 2001 . Facile deuteration of chiral N,N′‐substituted piperazines . Synthesis , : 235 – 238 .
   Google Scholar
• Santes , V. , Gómez , E. , Zárate , V. , Santillan , R. , Farfán , N. and Rojas‐Lima , S. 2001 . Synthesis of new homochiral 2,3‐dialkylpiperazines derived fron (R)‐(−)‐phenylglycinol . Tetrahedron: Asymmetry , 12 ( 2 ) : 241 – 247 .
   Google Scholar
• Sheldrick , G. M. “ SHELXL‐97, Program for Refinement of Crystal Structures ” . Germany : University of Göttingen .
   Google Scholar
• Hoffmann , D. and Meyer , J. F. 1961 . Überführung der 1‐4‐Benzoxazinone‐(2) in Phermorpholone (2) and N‐Substituierte Aminoalkohole . Chem. Ber. , 94 : 1676 – 1682 .
   Google Scholar
• Brown , D. W. , Ninan , A. and Sainsbury , M. 1997 . The synthesis of reduced phenoxazines as potential chain‐breaking antioxidants . Synthesis , : 895 – 898 .
   Google Scholar
• Mousseron , M. and Granger , R. 1947 . Etude des amino‐alcohols . Bull. Soc. Chim. Fr. , : 850 – 868 .
   Google Scholar