Synthesis of C₂-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring

REFERENCES

• Russo , A. ; Lattanzi , A. Asymmetric epoxidation of trans-chalcones organocatalyzed by β-amino alcohols . Eur. J. Org. Chem. 2008 , 2767 – 2773 .
   Web of Science ®Google Scholar
• Bergmeier , S. C. The synthesis of vicinal amino alcohols . Tetrahedron 2000 , 56 , 2561 .
   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
• Corey , E. H. ; Helal , C. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method . J. Angew. Chem., Int. Ed. Eng. 1998 , 37 , 1986 – 2102 .
   PubMed Web of Science ®Google Scholar
• Dondoni , A. ; Massi , M. Asymmetric organocatalysis: From infancy to adolescence . Angew. Chem. Int. Ed. 2008 , 47 , 4638 – 4660 .
   PubMed Web of Science ®Google Scholar
• Melchiorre , P. ; Marigo , M. ; Carlone , A. ; Bartoli , G. Asymmetric aminocatalysis—Gold rush in organic chemistry . Angew. Chem. Int. Ed. 2008 , 47 , 6138 – 6171 .
   PubMed Web of Science ®Google Scholar
• Denmark , S. E. ; Beutner G. L. Reviews, Lewis Base Catalysis in Organic Synthesis . Angew Chem. Int. Ed. 2008 , 47 , 1560 – 1638 .
   PubMed Web of Science ®Google Scholar
• Shen , Y.-M. ; Wang , B. ; Shi , Y. Communications. Enantioselective Synthesis of 2-ArylCyclopentanones by Asymmetric Epoxidation and Epoxide Rearrangement . Angew. Chem. Int. Ed. 2006 , 45 , 1429 – 1432 .
   PubMed Web of Science ®Google Scholar
• For recent general reviews: (a) Dalko P. I. ; Moisan , L. In the Golden Age of Organocatalysis . Angew. Chem. Int. Ed. 2004 , 43 , 5138 – 5175 ; (b) Special Issue on Asymmetric Organocatalysis . Acc. Chem. Res. 2004 , 37 ( 8 ), 487 .
   PubMed Web of Science ®Google Scholar
• Berkessel , A. ; Gröger , H. In Asymmetric Organocatalysis, Wiley-VCH, Weinheim; 2005.
   Google Scholar
• Sheldom , R. A. Chirotechnology , Marcel Dekker Inc , New York , 1993 .
   Google Scholar
• Kirkup , M. P. ; Rizvi , R. ; Shankar , B. B. ; Dugar , S. ; Clader , J. ; McCombie , S. W. ; Lin , S. ; Yumibe , N. ; Huie , K. ; Heek , M. ; Compton , D. S. ; Davis , H. R. ; McPhail , A. T. (−)-SCH 57939: Synthesis and pharmacological properties of a potent, metabolically stable cholesterol absorption inhibitor . Bioorg. Med. Chem. Lett. 1996 , 6 , 2069 .
   Web of Science ®Google Scholar
• For examples of asymmetric reductions of arlyoxy ketones, see: (a) Takahashi , H. ; Sakuraba , S. ; Takea , H. ; Achiwa , K. Asymmetric reactions catalyzed by chiral metal complexes.; (b) Highly efficient asymmetric hydrogenation of amino ketone derivatives leading to practical syntheses of (S)-propranolol and related compounds . J. Am. C hem. Soc. 1990 , 12 , 5877 .
   Google Scholar
• Gooding , O. ; Colin , B. ; Cooper , G. ; Jackson , D. ; Triply convergent synthesis of 15-(phenoxymethyl) and 4,5-allenyl prostaglandins. Preparation of an individual isomer of enprostil, . J. Org. Chem. 1993 , 58 , 3681 .
   Web of Science ®Google Scholar
• (a) Wang , Z. M. ; Zhang , X. L. ; Sharpless , K. B. Asymmetrıc Dıhydroxylatıon of aryl allyl Ethers . Tetrahedron Lett. 1993 , 34 , 2267 .; (b) Hanson , R. M. The synthetic methodology of nonracemic glycıdol and related 2,3-epoxy alcohols . Chem. Rev. 1991 , 91 , 439 .; (c) Larrow , J. F. ; Schaus , S. E. ; Jacobsen, E. N. Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN, an efficient, catalytic route to 1,2-amino alcohols . J. Am. Chem. Soc. 1996 , 118 , 7420 ;. (d) Kolb , H. C. ; VanNieuwenhze , M. S. ; Sharpless , K B. Asymmetric dihydroxylation . Chem. Rev. 1994 , 94 , 2483 .
   Web of Science ®Google Scholar
• Klunder , J. M. ; Ko , S. Y. ; Sharpless , K. B. Asymmetric epoxidation of allyl alcohol: Efficient routes to homochiral β-adrenergic blocking agents . J. Org. Chem. 1986 , 51 , 3710 .
   Web of Science ®Google Scholar
• (a) Tokunaga , M. ; Larrow , J. F. ; Kakiuchi , F. ; Jacobsen , E. N. Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis . Science 1997 , 277 , 936 .; (b) Brandes , B. D. ; Jacobsen , E. N. Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation/hydrolytic kinetic resolution sequence . Tetrahedron: Asymmetry 1997 , 8 , 3927 .
   PubMed Web of Science ®Google Scholar
• Furrow , M. E. ; Sehaus , S. E. ; Jacobsen , E. N. Practical synthesis of enantiomerically enriched glycidol by kinetic resolution of epichlorohydrin and dynamic kinetic resolution of epibromohydrin . Nucleus 1998 , 2 , 26 .
   Google Scholar
• (a) Corey , E. J. ; Shibata , S. ; Bakshi , R.-K. Advances in catalytic processes . J. Am. Chem. Soc. 1987 , 109 , 7925 – 7926 .; (b) Kagan , H.-B. ; Riant , O. Advances in catalytic processes . Chem. Rev. 1992 , 92 , 1007 – 1019 .
   Web of Science ®Google Scholar
• Turgut , Y. MSc thesis, Diyarbakir , 1998 .
   Google Scholar
• Turgut , Y. ; Demirel , N. ; Hosgoren , H. Synthesis of novel chiral C-2 symmetric diaza-18-crown-6 ether derivatives and their enantioselective recognition of amino acid derivatives . J. Inc. Phenoma and macrocyclic Chemistry , 2006 , 54 , 29 – 33 .
   Web of Science ®Google Scholar
• Huszthy , P. ; Oue , M. ; Bradshaw , J-S. ; Zhu , C-Y. ; Dalley , N-K. ; Curtis , J-C. ; Izatt , R-M. ; New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands . J. Org. Chem. 1992 , 57 , 5383 – 5394 .
   Web of Science ®Google Scholar
• Karakaplan , M. ; Turgut , Y. ; Hosgoren , H. A Practical synthesis of chiral 3-aryloxy-1,2- propanediols . Journal Of Chemical Research , 2005 , January 41 – 42 .
   Web of Science ®Google Scholar
• Horvath , G. ; Rusa , C. ; Köntös , Z. ; Gerencser , J. ; Huszthy , P. A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,6- Pyridinedicarboxylates . Synthetic Commun. 1999 , 29 ( 21 ), 3719 – 3731 .
   Web of Science ®Google Scholar