Catalytic enantioselective aryl transfer: Asymmetric addition of diphenylzine to aldehydes

Chemical Communications

Volumn , Issue 14, 1999, Pages 1295-1296

  Bolm, Carsten ^a   Muñiz, Kilian ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; OXAZOLINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY;

EID: 0039938946     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903884a     Document Type: Article

References (26)

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6. (a) For a pioneering report on an asymmetric phenylation in the presence of stoichiometric amounts of a chiral titanium-BINOL complex, see: D. Seebach, A. K. Beck, S. Roggo and A. Wonnacott, Chem. Ber., 1985, 118, 3673;
7. (b) For a later catalytic version employing Ti-TADDOLates, see: B. Weber and D. Seebach, Tetrahedron, 1994, 50, 7473.
8. P. I. Dosa, J. C. Ruble and G. C. Fu, J. Org. Chem., 1997, 62, 444.
9. 2 to prochiral ketones, see: P. I. Dosa and G. C. Fu, J. Am. Chem. Soc., 1998, 120, 445.
10. 2 additions to aldehydes: (a) K. Soai, Y. Kawase and A. Oshio, J. Chem. Soc., Perkin Trans. 1, 1991, 1613;
11. 2 species as had already been discussed in ref. 1 (c), 3.
12. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem. Int. Ed., 1998, 37, 3475.
13. (a) C. Bolm, K. Muñiz Fernández, A. Seger and G. Raabe, Synlett, 1997, 1051;
14. (b) C. Bolm, K. Muñiz Fernández, A. Seger, G. Raabe and K. Günther, J. Org. Chem., 1998, 63, 7860.
15. K. Muñiz Fernández, PhD thesis, RWTH Aachen, 1999.
16. C. Bolm, K. Muñiz and J. P. Hilderbrand, Org. Lett., in press.
17. 2 proved to be stable over a long period of time.
18. Recent examples of asymmetric autocatalyses: T. Shibata, S. Yonekubo and K. Soai, Angew. Chem., Int. Ed., 1999, 38, 659; T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai and K. Soai, J. Am. Chem. Soc., 1998, 120, 12 157 ; C. Bolm, A. Seger and F. Bienewald, Organic Synthesis Highlights III, ed. J. Mulzer and II. Waldmann, Wiley-VCH, Weinheim, 1998, p. 79.
19. Recent examples of asymmetric autocatalyses: T. Shibata, S. Yonekubo and K. Soai, Angew. Chem., Int. Ed., 1999, 38, 659; T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai and K. Soai, J. Am. Chem. Soc., 1998, 120, 12 157 ; C. Bolm, A. Seger and F. Bienewald, Organic Synthesis Highlights III, ed. J. Mulzer and II. Waldmann, Wiley-VCH, Weinheim, 1998, p. 79.
20. Recent examples of asymmetric autocatalyses: T. Shibata, S. Yonekubo and K. Soai, Angew. Chem., Int. Ed., 1999, 38, 659; T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai and K. Soai, J. Am. Chem. Soc., 1998, 120, 12 157 ; C. Bolm, A. Seger and F. Bienewald, Organic Synthesis Highlights III, ed. J. Mulzer and II. Waldmann, Wiley-VCH, Weinheim, 1998, p. 79.
21. 2 additions, see: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; C. Bolm, G. Schlingloff and K. Harms, Chem. Ber., 1992, 125, 1191.
22. 2 additions, see: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; C. Bolm, G. Schlingloff and K. Harms, Chem. Ber., 1992, 125, 1191.
23. C. Girard and H. B. Kagan, Angew. Chem., Int. Ed., 1998, 37, 2922; C. Bolm, Advanced Asymmetric Synthesis, ed. R. Stephenson, Capman and Hall, London, 1996, p. 9. M. Avalos, R. Babiano, P. Ciutas, J. L. Jiménez and J. C. Palacios, Tetrahedron: Asymmetry, 1997, 8, 2997.
24. C. Girard and H. B. Kagan, Angew. Chem., Int. Ed., 1998, 37, 2922; C. Bolm, Advanced Asymmetric Synthesis, ed. R. Stephenson, Capman and Hall, London, 1996, p. 9. M. Avalos, R. Babiano, P. Ciutas, J. L. Jiménez and J. C. Palacios, Tetrahedron: Asymmetry, 1997, 8, 2997.
25. C. Girard and H. B. Kagan, Angew. Chem., Int. Ed., 1998, 37, 2922; C. Bolm, Advanced Asymmetric Synthesis, ed. R. Stephenson, Capman and Hall, London, 1996, p. 9. M. Avalos, R. Babiano, P. Ciutas, J. L. Jiménez and J. C. Palacios, Tetrahedron: Asymmetry, 1997, 8, 2997.
26. To date, there is only one report on a non-linear effect (NLE) for a ferrocene ligand in an asymmetric diethylzinc addition: G. Nicolosi, A. Patti, R. Morrone and M. Piattelli, Tetrahedron: Asymmetry, 1994, 5, 1639.