Synthesis of C2-symmetric chiral amino alcohols: Their usage as organocatalysts for enantioselective opening of epoxide ring

Synthetic Communications

Volumn 40, Issue 22, 2010, Pages 3365-3377

  Turgut, Yilmaz ^a   Aral, Tarik ^a   Karakaplan, Mehmet ^a   Deniz, Pinar ^a   Hosgoren, Halil ^a  

^a DICLE UNIVERSITY   (Turkey)

Author keywords

Asymmetric ring opening; chiral amino alcohol; epoxide; organo catalysis

Indexed keywords

2 AMINOBUTANOL; AMINOALCOHOL; BETA AMINOALCOHOL; BIS(2,6 PYRIDYLDIMETHYL) 2 [N BENZYL]BUTAN 1 OL; BIS(2,6 PYRIDYLDIMETHYL) 2 AMINOBUTAN 1 OL; BIS(ALPHA,ALPHA' DIBROMO 2 XYLENE) 2 [N BENZYL]BUTAN 1 OL; BIS(ALPHA,ALPHA' DIBROMO 2 XYLENE) 2 AMINOBUTAN 1 OL; EPOXIDE; PROPYLENE GLYCOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; RING OPENING; SYNTHESIS;

EID: 77958029529     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903419878     Document Type: Article

References (31)

1. Russo, A.; Lattanzi, A. Asymmetric epoxidation of trans-chalcones organocatalyzed by b-amino alcohols. Eur. J. Org. Chem. 2008, 2767-2773.
2. Bergmeier, S. C. The synthesis of vicinal amino alcohols. Tetrahedron 2000, 56, 2561.
3. 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.
4. 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.
5. Dondoni, A.; Massi, M. Asymmetric organocatalysis: From infancy to adolescence. Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
6. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Asymmetric aminocatalysis\-Gold rush in organic chemistry. Angew. Chem. Int. Ed. 2008, 47, 6138-6171.
7. Denmark, S. E.; Beutner G. L. Reviews, Lewis Base Catalysis in Organic Synthesis. Angew Chem. Int. Ed. 2008, 47, 1560-1638.
8. 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.
9. Dalko P. I.; Moisan, L. In the Golden Age of Organoca-talysis. Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
10. Special Issue on Asymmetric Organocatalysis. Acc. Chem. Res. 2004, 37(8), 487.
11. Berkessel, A.; Groger, H. In Asymmetric Organocatalysis, Wiley-VCH, Weinheim; 2005.
12. Sheldom, R. A. Chirotechnology, Marcel Dekker Inc, New York, 1993.
13. 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.
14. 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.
15. 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.
16. 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.
17. Wang, Z. M.; Zhang, X. L.; Sharpless, K. B. Asymmetr?c D?hydroxylat?on of aryl allyl Ethers. Tetrahedron Lett. 1993, 34, 2267.
18. Hanson, R. M. The synthetic methodology of nonracemic glyc?dol and related 2,3-epoxy alcohols. Chem. Rev. 1991, 91, 439.
19. 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;.
20. Kolb, H. C; VanNieuwenhze, M. S.; Sharpless, K B. Asymmetric dihydroxylation. Chem. Rev. 1994, 94, 2483.
21. Klunder, J. M.; Ko, S. Y.; Sharpless, K. B. Asymmetric epoxidation of allyl alcohol: Efficient routes to homochiral (5-adrenergic blocking agents. J. Org. Chem. 1986, 51, 3710.
22. 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.
23. 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.
24. 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.
25. Corey, E. J.; Shibata, S.; Bakshi, R.-K. Advances in catalytic processes. J. Am. Chem. Soc. 1987, 109, 7925-7926.
26. (b)Kagan, H.-B.; Riant, O. Advances in catalytic processes. Chem. Rev. 1992, 92, 1007-1019.
27. Turgut, Y. MSc thesis, Diyarbakir, 1998.
28. 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.
29. 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.
30. Karakaplan, M.; Turgut, Y.; Hosgoren, H. A Practical synthesis of chiral 3-aryloxy-1,2-propanediols. Journal Of Chemical Research, 2005, January 41-42.
31. Horvath, G.; Rusa, C; Kontos, Z.; Gerencser, J.; Huszthy, P. A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,6-Pyridinedicarbox-ylates. Synthetic Commun. 1999, 29(21),3719-3731.