Enantioselective PTC: Varying the cinchona alkaloid motive

Tetrahedron

Volumn 55, Issue 20, 1999, Pages 6335-6346

  Dehmlow, Eckehard Volker ^a   Wagner, Stefan ^a   Müller, Achim ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; ENANTIOMER; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033553461     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00210-0     Document Type: Article

References (24)

1. 1. Applications of Phase Transfer Catalysis, Part 69.-For part 68, see: E.V. Dehmlow, R. Klauck, B. Neumann, H.G. Stammler, J. Prakt. Chem. 1998, 340, 572.
2. 2. T. Shioiri, "Chiral Phase Transfer Catalysis" in Handbook of Phase Transfer Catalysis, Y. Sasson and R. Neumann, edits., Blackie Academ. & Professional, London, 1997, pp. 462-479.
3. 3. M. J. O'Donnell, "Asymmetric Phase Transfer Reactions" in Catalytic Asymmetric Synthesis, I. Ojima, edit., VCH-Publ., New York, Weinheim, 1993, pp.389-411.
4. 4. E.V. and S.S. Dehmlow, "Phase Transfer Catalysis", 3rd rev., enl. edit., VCH-Publ., Weinheim, New York, 1993, pp. 80-90.
5. 5. D. L. Hughes, U.-H. Dolling, K. M. Ryan, E. F. Schoenewaldt, E. J. J. Grabowski, J. Org. Chem. 1987, 52, 4745 and previous publications.
6. 6. T. B. K. Lee, G. S. K. Wong, J. Org. Chem. 1991, 56, 872.
7. 7. M. J. O'Donnell, Z. Fang, X. Ma, J. C. Huffman, Heterocycles 1997, 46, 617 and previous publications
8. 8. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595.
9. 9. E. J. Corey, F. Xu, M. C. Noe, J. Amer. Chem. Soc. 1997, 119, 12414.
10. 10. A. Ando, T. Miura, T. Tatematsu, T. Shioiri, Tetrahedron Lett. 1993, 34, 1507.
11. 11. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599.
12. 12. M. Masui, A. Ando, T. Shioiri, Tetrahedron Lett. 1988, 29, 2835.
13. 13. Pivalophenone reduction yields 27% e.e. with QUIBEC: Dissertation R. Klauck, U. of Bielefeld, 1997. A singular catalyst reaches 39.5% e.e.: E. V. Dehmlow, S. Schrader, Pol. J. Chem. 1994, 68, 2199.
14. 13. Pivalophenone reduction yields 27% e.e. with QUIBEC: Dissertation R. Klauck, U. of Bielefeld, 1997. A singular catalyst reaches 39.5% e.e.: E. V. Dehmlow, S. Schrader, Pol. J. Chem. 1994, 68, 2199.
15. 14. S. Arai, T. Shioiri, Tetrahedron Lett. 1998, 39, 2145.
16. 15. W. Nerinckx, M. Vandewalle, Tetrahedron: Asymmetry 1990, 1, 265.
17. 16. R. S. E. Conn, A. V. Lovell, S. Karady, L. M. Weinstock, J. Org. Chem. 1986, 51, 4710.
18. 17. E. V. Dehmlow, R. Klauck, S. Düttmann, B. Neumann, H.-G. Stammler, Tetrahedron. Asymmetry 1998, 9, 2235.
19. 18. E. V. Dehmlow, R. Klauck, B. Neumann, H.-G. Stammler, J. Prakt. Chem. 1998, 340, 572 and previous publications.
20. 19. H. M. R. Hoffmann, T. Plessner, C. von Riesen, Synlett 1996, 690.
21. 20. J. P. Begue, M. Fetizon, Bull. Chim. Fr. 1969, 1251.
22. 21. V. Braschler, C. A. Grob, A. Kaiser, Helv. Chim. Acta 1963, 46, 2646.
23. 22. K. Koch, J. H. Smitrovich, Tetrahedron Lett. 1994, 35, 1137.
24. 23. QUIBEC = N-benzylquininium Cl, BCDC: = N-benzyl-cinchonidinium Cl, BCNC = N-benzyl-cinchonium Cl.