Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of β-cyclodextrin

Chirality

Volumn 11, Issue 7, 1999, Pages 541-545

  Doussot, Joël ^a   Guy, Alain ^a   Siaugue, Jean Michel ^a   Ferroud, Clotilde ^a   Guieres, Annie Fal ^a  

^a CNRS   (France)

Author keywords

Chemistry in aqueous medium; Hydrogen bonding; Hydrophobic interactions; Inclusion complexes; Regio and stereocontrol; Solid state reaction

Indexed keywords

BETA CYCLODEXTRIN; BORANE DERIVATIVE; EPOXIDE; STYRENE OXIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; HYDROGEN BOND; HYDROPHOBICITY; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 0032803679     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:7<541::AID-CHIR5>3.0.CO;2-G     Document Type: Article

References (26)

1. (a) Stinson SC. Chiral Drugs. Chem Eng News 1992;Sept 28:46-78. Stinson SC. Chiral Drugs. Chem Eng News 1993;Sept 27:38-64. Stinson SC. Chiral Drugs. Chem Eng News 1994;Sept 19:38-72. Stinson SC. Chiral Drugs. Chem Eng News 1995;0ct 9:44-74.
2. (a) Stinson SC. Chiral Drugs. Chem Eng News 1992;Sept 28:46-78. Stinson SC. Chiral Drugs. Chem Eng News 1993;Sept 27:38-64. Stinson SC. Chiral Drugs. Chem Eng News 1994;Sept 19:38-72. Stinson SC. Chiral Drugs. Chem Eng News 1995;0ct 9:44-74.
3. (a) Stinson SC. Chiral Drugs. Chem Eng News 1992;Sept 28:46-78. Stinson SC. Chiral Drugs. Chem Eng News 1993;Sept 27:38-64. Stinson SC. Chiral Drugs. Chem Eng News 1994;Sept 19:38-72. Stinson SC. Chiral Drugs. Chem Eng News 1995;0ct 9:44-74.
4. (a) Stinson SC. Chiral Drugs. Chem Eng News 1992;Sept 28:46-78. Stinson SC. Chiral Drugs. Chem Eng News 1993;Sept 27:38-64. Stinson SC. Chiral Drugs. Chem Eng News 1994;Sept 19:38-72. Stinson SC. Chiral Drugs. Chem Eng News 1995;Oct 9:44-74.
5. (b) Crossley R. The relevance of chirality to the study of biological activity. Tetrahedron Rep 1992;48:8155-8178.
6. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem Rev 1998;98:1743-1753.
7. (a) Bender ML, Koniyama M. 1978 In: Cyclodextrin Chemistry. New-York: Springer-Verlag; 1978.
8. (b) Szejtli J. In: Cyclodextrin and their inclusion complexes. Budapest: Akademiai Kiado; 1982.
9. (c) Szejtli J. The properties and potential uses of cyclodextrin derivatives. J Inclusion Phenom 1992;14:25-36.
10. (d) Li S, Purdy WC. Cyclodextrins and their applications in analytical chemistry. Chem Rev 1992;92:1457-1470.
11. (e) Wenz G. Cyclodextrins as building blocks for supramolecular structures and functional units. Angew Chem, Int Ed Eng 1994;33:803-822.
12. (a) Takahashi K, Hallori K. Asymmetric reactions with cyclodextrins. J Inclusion Phenom 1994;17:1-24.
13. (b) Kano K. Selectivities in cyclodextrin chemistry. Bioorg Chem Front. 1993;3:1-23.
14. (c) Divakar S, Maheswaran M. Applications of cyclodextrins in organic syntheses. J Sci Ind Res 1994;53:924-932.
15. (d) Takahashi K. Organic reactions mediated by cyclodextrins. Chem Rev 1998;98:2013-2033.
16. Easton CJ, Lincoln SF. Chiral discrimination by modified cyclodextrins. Chem Soc Rev 1996;163-170.
17. 4 in aqueous media. Bull Chem Soc Jpn 1992;65:2690-2696.
18. 4 in the presence of β-cyclodextrin. Chirality 1994;6:658-664.
19. (c) Hu H, Uno M, Harada A, Takahashi S. Selective ring-opening reaction of epoxides with sodium borohydride in the presence of cyclodextrins in aqueous media. Chem Lett 1990;797-798.
20. (d) Hu H, Uno M, Harada A, Takahashi S. Selective ring-opening reaction of epoxides with sodium borohydride in the presence of cyclodextrins in aqueous media. Bull Chem Soc Jpn 1991;64:1884-1888.
21. Doussot J, Guy A, Garreau R, Falguières A, Cossy J, Amsterdamsky C. Préparation sélective d'alcools benzyliques substitués à partir de substrats aromatiques complexes dans la β-cyclodextrine. Bull Soc Chim Fr 1996; 133:161-166.
22. Corey EJ, Chaykowsky MJ. Dimethyloxosulfonium methylide and dimethylsulfonium methylide. Formation and applications to organic synthesis. J Am Chem Soc 1965;87:1353-1364.
23. Rekker RF, Mannhold R. Calculation of Drug Lipophilicity. Weinheim: VCH; 1992.
24. Toda F, Shigemasa T. Enantioselective reduction of ketones in inclusion complexes with cyclomaltoheptaosee in the solid state: Acceleration of the reaction by ultrasound. Carbohydrate Res 1989;192:363-365.
25. (a) Guy A, Doussot J, Garreau R, Godefroy-Falguières A. Selective ring-opening reaction of styrene oxide with lithium azide in the presence of cyclodextrins in aqueous media. Tetrahedron: Asymmetry 1992;3:247-250.
26. (b) Doussot J, Guy A, Dallamaggiore A, Garreau R. Ouverture sélective d'époxydes styréniques substitués à l'aide d'azoture de lithium en présence de β-cyclodextrine. Can J Chem 1995; 73:599-603.