First catalytic, enantioselective aldol-tishchenko reactions with ketone aldols as enol equivalents

Synlett

Volumn , Issue 6, 2003, Pages 837-840

  Schneider, Christoph ^a   Hansch, Markus ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Aldol reaction; Asymmetric catalysis; Ketone aldols; Tishchenko reduction; Zirconium

Indexed keywords

ACETONYLACETONE; ALDEHYDE; KETONE DERIVATIVE; ZIRCONIUM;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION;

EID: 0038293485     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38741     Document Type: Article

References (41)

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3. For reviews see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (d) Carreira, E. M. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 998. (e) Gröger, H.; Vogel, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
4. For reviews see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (d) Carreira, E. M. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 998. (e) Gröger, H.; Vogel, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
5. For reviews see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (d) Carreira, E. M. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 998. (e) Gröger, H.; Vogel, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
6. For reviews see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (d) Carreira, E. M. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 998. (e) Gröger, H.; Vogel, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
7. For reviews see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (d) Carreira, E. M. Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 998. (e) Gröger, H.; Vogel, E. M.; Shibasaki, M. Chem.-Eur. J. 1998, 4, 1137. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
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19. A slightly different approach was pursued by Feringa, Alexakis, and Krische who investigated catalytic, enantioselective conjugate additions to enones followed by a diastereoselective aldol reaction, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620; Angew. Chem. 1997, 109, 2733. (b) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (c) Cauble, D. F.; Gipson, J.D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
20. A slightly different approach was pursued by Feringa, Alexakis, and Krische who investigated catalytic, enantioselective conjugate additions to enones followed by a diastereoselective aldol reaction, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620; Angew. Chem. 1997, 109, 2733. (b) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (c) Cauble, D. F.; Gipson, J.D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
21. A slightly different approach was pursued by Feringa, Alexakis, and Krische who investigated catalytic, enantioselective conjugate additions to enones followed by a diastereoselective aldol reaction, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620; Angew. Chem. 1997, 109, 2733. (b) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (c) Cauble, D. F.; Gipson, J.D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
22. A slightly different approach was pursued by Feringa, Alexakis, and Krische who investigated catalytic, enantioselective conjugate additions to enones followed by a diastereoselective aldol reaction, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620; Angew. Chem. 1997, 109, 2733. (b) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (c) Cauble, D. F.; Gipson, J.D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
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27. (a) Simpura, I.; Nevalainen, V. Angew. Chem. Int. Ed. 2000, 39, 3422; Angew. Chem. 2000, 112, 3564.
28. (b) Nevalainen, V.; Simpura, I. Tetrahedron Lett. 2001, 42, 3905.
29. Evans et al. have established metal-catalyzed, highly anti-diastereoselective Tishchenko reductions of β-hydroxy ketones, see: Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
30. For a comprehensive review about synthesis and various applications of tartaric acid-derived TADDOLs as chiral ligands and auxiliaries see: Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem. Int. Ed. 2001, 40, 92; Angew. Chem. 2001, 113, 97 and ref. cited therein.
31. For a comprehensive review about synthesis and various applications of tartaric acid-derived TADDOLs as chiral ligands and auxiliaries see: Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem. Int. Ed. 2001, 40, 92; Angew. Chem. 2001, 113, 97 and ref. cited therein.
32. 3 (244.37): C 68.81, H 11.55; Found: C 69.08, 11.29.
33. 3-reduction of the corresponding aldol products which were obtained according to the following references: List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
34. (b) In addition see: Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497.
35. (c) Also see: Ramachandran, P. V.; Xu, W.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4911.
36. (d) The absolute configuration of the diol derived from 9b was assigned based upon the known rotation value, see: Marinetti, A.; Genet, J.-P.; Jus, S.; Blanc, D.; Ratovelomanana-Vidal, V. Chem.-Eur. J. 1999, 5, 1160.
37. (e) The absolute configuration of all other products was assigned in analogy to these experiments
38. 2-BINOL: 89% yield (28% ee).
39. 4
40. For an excellent review about nonlinear effects see: Girard, C.; Kagan, H. B. Angew. Chem. Int. Ed. 1998, 37, 2922; Angew. Chem. 1998, 110, 3089.
41. For an excellent review about nonlinear effects see: Girard, C.; Kagan, H. B. Angew. Chem. Int. Ed. 1998, 37, 2922; Angew. Chem. 1998, 110, 3089.