Stereoselective 2-hydroxy-1,2,2-triphenylethyl propionate-based aldol additions to ketones

Synlett

Volumn , Issue 10, 1999, Pages 1600-1602

  Braun, Manfred ^a   Mai, Brigitte ^a   Ridder, Daniel M ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Aldol reaction; Asymmetric synthesis; Ketones; Tertiary alcohols; Titanium

Indexed keywords

ALCOHOL DERIVATIVE; CARBOXYLIC ACID; KETONE DERIVATIVE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0032823628     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2885     Document Type: Article

References (31)

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3. b) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. 1985, 97, 1; Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
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6. c) Braun, M. Angew. Chem. 1987, 99, 24; Angew. Chem. Int. Ed. Engl. 1987, 26, 24.
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8. e) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Chapter 1.7.
9. f) Paterson, I. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds; Pergamon: Oxford, 1991; Chapter 1.9.
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12. For rewies, see: Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Chapter 7.2. Gröger, H.; Vogl, E.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
13. For rewies, see: Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Chapter 7.2. Gröger, H.; Vogl, E.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
14. For rewies, see: Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Chapter 7.2. Gröger, H.; Vogl, E.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
15. Acetate enolate equivalents have been added to ketones with moderate stereoselectivity in most cases: Guetté, M.; Capillon, J.; Guetté, J.-P. Tetrahedron 1973, 29, 3659. Dongala, E. B.; Dull, D. L.; Mioskowski, C.; Solladié, G. Tetrahedron Lett. 1973, 4983. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227.
16. Acetate enolate equivalents have been added to ketones with moderate stereoselectivity in most cases: Guetté, M.; Capillon, J.; Guetté, J.-P. Tetrahedron 1973, 29, 3659. Dongala, E. B.; Dull, D. L.; Mioskowski, C.; Solladié, G. Tetrahedron Lett. 1973, 4983. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227.
17. Acetate enolate equivalents have been added to ketones with moderate stereoselectivity in most cases: Guetté, M.; Capillon, J.; Guetté, J.-P. Tetrahedron 1973, 29, 3659. Dongala, E. B.; Dull, D. L.; Mioskowski, C.; Solladié, G. Tetrahedron Lett. 1973, 4983. Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227.
18. Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069. Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893. Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
19. Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069. Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893. Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
20. Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1989, 2069. Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893. Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
21. Mukaiyama, T. Org. React. N. Y. 1982, 28, 203.
22. See ref. 2c,g for an elucidation of these terms.
23. Sacha, H.; Waldmüller, D.; Braun, M. Chem. Ber. 1994, 127, 1959.
24. Braun, M.; Gräf, S.; Herzog, S. Org. Synth. 1993, 72, 32.
25. Crystallographic data (excluding structrue factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-122182. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: Int. code +(44)1223-336033; e-mail: deposit@ccdc.cam.ac.uk).
26. Cf. Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford 1991; Chapter 1.10. We are aware that, according to this transition state model, the diastereoselectivity of the aldol addition should reflect the E : Z ratio of the silyl ketene acetal. Since, however, the mixture (87 :13) of E-and Z-silyl ketene acetal is used in excess (1,3 mol%), one might assume the E-isomer to react predominantly. On the other hand, open transition state models could also be taken into account; Cf. Oppolzer, W.; Marco-Contelles, J. Helv.Chim.Acta 1986, 69, 1699.
27. Cf. Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford 1991; Chapter 1.10. We are aware that, according to this transition state model, the diastereoselectivity of the aldol addition should reflect the E : Z ratio of the silyl ketene acetal. Since, however, the mixture (87 :13) of E-and Z-silyl ketene acetal is used in excess (1,3 mol%), one might assume the E-isomer to react predominantly. On the other hand, open transition state models could also be taken into account; Cf. Oppolzer, W.; Marco-Contelles, J. Helv.Chim.Acta 1986, 69, 1699.
28. Braun, M. Angew. Chem. 1996, 108, 565; Angew. Chem. Int. Ed. Engl. 1996, 35, 519.
29. Braun, M. Angew. Chem. 1996, 108, 565; Angew. Chem. Int. Ed. Engl. 1996, 35, 519.
30. f= 0,5 (n-hexane/ethyl acetate 5 : 1).
31. 3)], 136.2 (=CH), 180.6 (CO).