A SuperQuat glycolate aldol approach to the asymmetric synthesis of hexose monosaccharides

Organic and Biomolecular Chemistry

Volumn 3, Issue 2, 2005, Pages 348-359

  Davies, Stephen G ^a   Nicholson, Rebecca L ^a   Smith, Andrew D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; CATALYSTS; CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DIELS-ALDRICH REACTION; LEWIS ACID; MONOSACCHARIDE;

STEREOCHEMISTRY;

ALDEHYDE; GLYCOLIC ACID DERIVATIVE; HEXOSE; MONOSACCHARIDE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; GLYCOLATES; HEXOSES; MOLECULAR CONFORMATION; MONOSACCHARIDES; STEREOISOMERISM;

EID: 12844275972     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415943h     Document Type: Article

References (112)

1. This approach has been extensively used; for example, in the synthesis of the rare sugar L-gulose from L-xylose; see: A. Dondoni, A. Marra and A. Massi, J. Org. Chem., 1997, 62, 6261.
2. (a) M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 1983, 105, 6968;
3. (b) S. J. Danishefsky, E. Larson and J. P. Springer, J. Am. Chem. Soc., 1985, 107, 1274;
4. (c) S. J. Danishefsky, W. H. Pearson and B. E. Segmuller, J. Am. Chem. Soc., 1985, 107, 1280;
5. (d) M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 1986, 108, 7060;
6. (e) S. E. Schaus, J. Branalt and E. N. Jacobsen, J. Org. Chem., 1998, 63, 403.
7. (a) J. M. Harris, M. D. Keranen and G. A. O'Doherty, J. Org. Chem., 1999, 64, 2982;
8. (b) J. M. Harris, M. D. Keränen, H. Nguyen, V. G. Young and G. A. O'Doherty, Carbohydr. Res., 2000, 328, 17;
9. (c) I. Henderson, K. B. Sharpless and C.-H. Wong, J. Am. Chem. Soc., 1994, 116, 558;
10. (d) S. Kobayashi and T. Kawasuji, Synlett, 1993, 911:
11. (e) M. Takeuchi, T. Taniguchi and K. Ogasawara, Synthesis, 1999, 341;
12. (f) T. Taniguchi, M. Takeuchi, K. Kadota, A. S. ElAzab and K. Ogasawara, Synthesis, 1999, 1325;
13. (g) M. Takeuchi, T. Taniguchi and K. Ogasawara, Chirality, 2000, 338.
14. (a) For a review, see: H. J. M. Gijsen, L. Qiao, W. Fitz and C.-H. Wong, Chem. Rev., 1996, 96, 443;
15. (b) T. Hudlicky, K. K. Pitzer, M. R. Stabile, A. J. Thorpe and G. M. Whited, J. Org. Chem., 1996, 61, 4151;
16. (c) C. R. Johnson, A. Golebiowski and D. H. Steensma, J. Am. Chem. Soc., 1992, 114, 9414.
17. (a) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabusa, Tetrahedron, 1990, 46, 265;
18. (b) J. A. Marshall, B. M. Seletsky and G. P. Luke. J. Org. Chem., 1994, 59, 3413;
19. (c) J. A. Marshall and K. W. Hinkle, J. Org. Chem., 1996, 61, 105.
20. H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Joørgensen, J. Org. Chem., 2000, 65, 4487.
21. (a) S. Y. Koo, A. W. M. Lee, S. Masamune, L. A. Reed III, K. B. Sharpless and F. J. Walker, Science, 1983, 220, 949;
22. (b) S. Y. Koo, A. W. M. Lee, S. Masamune, L. A. Reed III, K. B. Sharpless and F. J. Walker, Tetrahedron. 1990, 46, 245.
23. For selected examples of the recent use of the aldol reaction for the synthesis of carbohydrates and their derivatives, see: (a) D. A. Evans, E. Hu and J. S. Tedrow, Org. Letts., 2001, 3, 3133; (b) M. P. Sibi, J. Lu and J. Edwards, J. Org. Chem., 1997, 62, 5864.
24. For selected examples of the recent use of the aldol reaction for the synthesis of carbohydrates and their derivatives, see: (a) D. A. Evans, E. Hu and J. S. Tedrow, Org. Letts., 2001, 3, 3133; (b) M. P. Sibi, J. Lu and J. Edwards, J. Org. Chem., 1997, 62, 5864.
25. M. Majewski and P. Nowak, J. Org. Chem., 2000, 65, 5152.
26. S. Kobayashi and T. Kawasuji, Synlett, 1993, 911.
27. (a) For an excellent review on asymmetric aldol reactions with boron enolates, see: C. J. Cowden and I. Paterson, Org. React., 1997, 51, 1;
28. (b) For a review of the rational design of enol borinates, see: A. Bernardi, C. Gennari, J. M. Goodman and I. Paterson, Tetrahedron: Asymmetry, 1995, 6, 2613;
29. For the preparation of all possible diastereoisomeric combinations from a single aldol reagent, see: N. A. Van Draanen, S. Arseniyadis, M. T. Crimmins and C. H. Heathcock, J. Org. Chem., 1991, 56, 2499;
30. For the development of oxazolidinone auxiliary aldol reactions, see: D. A. Evans, J. Bartroli and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127;
31. (e) D. A. Evans, D. L. Rieger, M. T. Bilodeau and F. Urpi, J. Am. Chem. Soc., 1991, 113, 1047;
32. (f) D. A. Evans and J. V. Nelson, Top. Stereochem., 1982, 13. 111;
33. (g) D. A. Evans, J. S. Tedrow, J. T. Shaw and C. W. Downey, J. Am. Chem. Soc., 2002, 124, 392.
34. For selected examples, see: (a) S. R. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis and M. Hartmann, Tetrahedron, 1996, 52, 3229: (b) J. D. White and J. Deerberg, Chem. Commun., 1997, 1919: (c) S. Kobayashi and T. Furuta, Tetrahedron, 1998, 54, 10275: (d) M. B. Andrus, E. L. Meredith and B. B. V. Soma Sekhar, Org. Lett., 2001, 3, 259; (e) C. J. Forsyth, J. Hao and J. Aiguade, Angew, Chem., Int. Ed., 2001, 40, 3663.
35. For selected examples, see: (a) S. R. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis and M. Hartmann, Tetrahedron, 1996, 52, 3229: (b) J. D. White and J. Deerberg, Chem. Commun., 1997, 1919: (c) S. Kobayashi and T. Furuta, Tetrahedron, 1998, 54, 10275: (d) M. B. Andrus, E. L. Meredith and B. B. V. Soma Sekhar, Org. Lett., 2001, 3, 259; (e) C. J. Forsyth, J. Hao and J. Aiguade, Angew, Chem., Int. Ed., 2001, 40, 3663.
36. For selected examples, see: (a) S. R. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis and M. Hartmann, Tetrahedron, 1996, 52, 3229: (b) J. D. White and J. Deerberg, Chem. Commun., 1997, 1919: (c) S. Kobayashi and T. Furuta, Tetrahedron, 1998, 54, 10275: (d) M. B. Andrus, E. L. Meredith and B. B. V. Soma Sekhar, Org. Lett., 2001, 3, 259; (e) C. J. Forsyth, J. Hao and J. Aiguade, Angew, Chem., Int. Ed., 2001, 40, 3663.
37. For selected examples, see: (a) S. R. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis and M. Hartmann, Tetrahedron, 1996, 52, 3229: (b) J. D. White and J. Deerberg, Chem. Commun., 1997, 1919: (c) S. Kobayashi and T. Furuta, Tetrahedron, 1998, 54, 10275: (d) M. B. Andrus, E. L. Meredith and B. B. V. Soma Sekhar, Org. Lett., 2001, 3, 259; (e) C. J. Forsyth, J. Hao and J. Aiguade, Angew, Chem., Int. Ed., 2001, 40, 3663.
38. For selected examples, see: (a) S. R. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis and M. Hartmann, Tetrahedron, 1996, 52, 3229: (b) J. D. White and J. Deerberg, Chem. Commun., 1997, 1919: (c) S. Kobayashi and T. Furuta, Tetrahedron, 1998, 54, 10275: (d) M. B. Andrus, E. L. Meredith and B. B. V. Soma Sekhar, Org. Lett., 2001, 3, 259; (e) C. J. Forsyth, J. Hao and J. Aiguade, Angew, Chem., Int. Ed., 2001, 40, 3663.
39. (a) B. Loubinoux, J.-L. Sinnes, A. C. O'Sullivan and T. Winkler, Helv. Chim. Acta., 1995, 78, 122;
40. (b) J. M. C. Golec and S. D. Jones, Tetrahedron Lett., 1993, 50, 8159;
41. (c) D. A. Evans, S. J. Miller, M. D. Ennis and P. L. Ornstein, J. Org. Chem., 1992, 57, 1067.
42. For leading examples of iterative aldol approaches to polypropionate fragments on solid phase, see: (a) I. Pater son, M. Donghi and K. Gerlach, Angew. Chem. Int. Ed., 2000, 39, 3315; (b) M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 38, 6851; (c) For solution phase synthesis, see: I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 42, 7441; (d) I. Paterson and J. P. Scott, J. Chem. Soc., Perkin Trans. 1., 1999, 1003.
43. For leading examples of iterative aldol approaches to polypropionate fragments on solid phase, see: (a) I. Pater son, M. Donghi and K. Gerlach, Angew. Chem. Int. Ed., 2000, 39, 3315; (b) M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 38, 6851; (c) For solution phase synthesis, see: I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 42, 7441; (d) I. Paterson and J. P. Scott, J. Chem. Soc., Perkin Trans. 1., 1999, 1003.
44. For leading examples of iterative aldol approaches to polypropionate fragments on solid phase, see: (a) I. Pater son, M. Donghi and K. Gerlach, Angew. Chem. Int. Ed., 2000, 39, 3315; (b) M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 38, 6851; (c) For solution phase synthesis, see: I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 42, 7441; (d) I. Paterson and J. P. Scott, J. Chem. Soc., Perkin Trans. 1., 1999, 1003.
45. For leading examples of iterative aldol approaches to polypropionate fragments on solid phase, see: (a) I. Pater son, M. Donghi and K. Gerlach, Angew. Chem. Int. Ed., 2000, 39, 3315; (b) M. Reggelin and V. Brenig, Tetrahedron Lett., 1996, 38, 6851; (c) For solution phase synthesis, see: I. Paterson and J. P. Scott, Tetrahedron Lett., 1997, 42, 7441; (d) I. Paterson and J. P. Scott, J. Chem. Soc., Perkin Trans.1., 1999, 1003.
46. S. Kobayashi, T. Wakabayashi and M. Yasuda, J. Org. Chem., 1998, 63, 4868.
47. (a) A. B. Northrup, I. K. Mangion, F. Hettche and D. W. C. MacMillan, Angew. Chem., Int. Ed., 2004, 43, 2152; (b) For a related protocol, see: R. I. Storer and D. W. C. MacMillan, Tetrahedron, 2004, 60, 7705.
48. (a) A. B. Northrup, I. K. Mangion, F. Hettche and D. W. C. MacMillan, Angew. Chem., Int. Ed., 2004, 43, 2152; (b) For a related protocol, see: R. I. Storer and D. W. C. MacMillan, Tetrahedron, 2004, 60, 7705.
49. A. B. Northrup and D. W. C. MacMillan, Science, 2004, 305, 1752.
50. For our previous related work in this area with achiral oxazolidinones, see: (a) J. Bach, S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Tetrahedron Lett., 1999, 40, 6677; (b) J. Bach, C. Blachere, S. D. Bull, S. G. Davies, R. L. Nicholson, P. D. Price, H. J. Sanganee and A. D. Smith, Org. BioMol. Chem., 2003, 2001; (c) For our studies with chiral oxazolidinones, see: S. D. Bull, S. G. Davies, R. L. Nicholson and A. D. Smith, Tetrahedron: Asymmetry, 2000, 13, 3475; (d) S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Org. Biomol. Chem., 2003, 2886.
51. For our previous related work in this area with achiral oxazolidinones, see: (a) J. Bach, S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Tetrahedron Lett., 1999, 40, 6677; (b) J. Bach, C. Blachere, S. D. Bull, S. G. Davies, R. L. Nicholson, P. D. Price, H. J. Sanganee and A. D. Smith, Org. BioMol. Chem., 2003, 2001; (c) For our studies with chiral oxazolidinones, see: S. D. Bull, S. G. Davies, R. L. Nicholson and A. D. Smith, Tetrahedron: Asymmetry, 2000, 13, 3475; (d) S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Org. Biomol. Chem., 2003, 2886.
52. For our previous related work in this area with achiral oxazolidinones, see: (a) J. Bach, S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Tetrahedron Lett., 1999, 40, 6677; (b) J. Bach, C. Blachere, S. D. Bull, S. G. Davies, R. L. Nicholson, P. D. Price, H. J. Sanganee and A. D. Smith, Org. BioMol. Chem., 2003, 2001; (c) For our studies with chiral oxazolidinones, see: S. D. Bull, S. G. Davies, R. L. Nicholson and A. D. Smith, Tetrahedron: Asymmetry, 2000, 13, 3475; (d) S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Org. Biomol. Chem., 2003, 2886.
53. For our previous related work in this area with achiral oxazolidinones, see: (a) J. Bach, S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Tetrahedron Lett., 1999, 40, 6677; (b) J. Bach, C. Blachere, S. D. Bull, S. G. Davies, R. L. Nicholson, P. D. Price, H. J. Sanganee and A. D. Smith, Org. BioMol. Chem., 2003, 2001; (c) For our studies with chiral oxazolidinones, see: S. D. Bull, S. G. Davies, R. L. Nicholson and A. D. Smith, Tetrahedron: Asymmetry, 2000, 13, 3475; (d) S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee and A. D. Smith, Org. Biomol. Chem., 2003, 2886.
54. S. G. Davies, I. A. Hunter, R. L. Nicholson, P. M. Roberts, E. D. Savory and A. D. Smith, Tetrahedron, 2004, 60, 7553.
55. S. G. Davies, R. L. Nicholson and A. D. Smith, Org. Biomol. Chem., 2004, 3385.
56. S. G. Davies, R. L. Nicholson and A. D. Smith, Synlett, 2002, 1637.
57. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
58. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
59. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
60. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
61. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
62. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
63. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
64. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
65. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
66. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
67. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
68. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
69. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
70. For other selected asymmetric glycolate enolate reactions, see: (a) M. T. Crimmins, K. A. Emmitte and J. D. Katz, Org. Lett., 2000, 2, 2165; M. T. Crimmins and M. T. Powell, J. Am. Chem. Soc, 2003, 125, 7592; S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626; D. Enders and U. Reinhold, Synlett, 1994, 63, 792; D. Enders and U. Reinhold, Angew. Chem., Int. Ed. Engl., 1995, 34, 1219; D. Enders and U. Reinhold, Liebigs Ann., 1996, 34, 11; (b) For glycolate enolate additions to acyclic ketimines, see: P. Bravo, S. Fustero, M. Guidetti, A. Volonterio and M. Zanda, J. Org. Chem., 1999, 64, 8731; (c) For representative examples of other glycolate aldol reactions, see: W. R. Roush, L. A. Pfeifer and T. G. Marron, J. Org. Chem., 1998, 63, 2064; K. S. Kim and S. D. Hong, Tetrahedron Letts., 2000, 41, 5909; S. Sasaki, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1999, 40, 3187; M. B. Andrus, B. B. V. Soma Sekhar, T. M. Turner and E. L. Meredith, Tetrahedron Lett., 2001, 42, 7197; C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti and A. Vulpetti, J. Org. Chem., 1997, 62, 4746; M. T. Crimmins, B. W. King, W. J. Zuercher and A. L. Choy, J. Org. Chem., 2000, 65, 8499; A. Bierstedt, J. Roels, J. Zhang, Y. Wang, R. Fröhlich and P. Metz, Tetrahedron Lett., 2003, 44, 7867.
71. (a) The syn-configuration within 5 and 6 was assigned upon the well-precedented assumption that the C(3')-hydroxycarbonyl aldol products exist in solution predominantly in an intramolecularly hydrogen bonded form, resulting in α,β usually in the range of 2-6 Hz for syn-aldol products and 7-10 Hz for anti-aldol products. For leading references, see: M. Stiles, R. W. Winkler, Y.-L. Chang and L. Traynor, J. Am. Chem. Soc., 1964, 86, 3337;
72. (b) H. O. House, D. S. Crumrine, A. Y. Teranishi and H. D. Olmstead, J. Am. Chem. Soc., 1973, 95, 3310;
73. (c) C. H. Heathcock, M. C. Pirrung and J. E. Sohn, J. Org. Chem., 1980, 45, 1066;
74. C.H. Heathcock, C.T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn and J. Lampe, J. Org. Chem., 1979, 44, 4294.
75. Previous work within this area has shown that direct DIBAL-H reduction of unprotected aldol products result in a complex mixture of products; see ref. 19.
76. (a) For a study concerned with the stability of related N-acyl hemi-aminals, see:M. P. DeNinno and C. Eller, Tetrahedron Lett., 1997, 38, 6545;
77. (b) M. P. DeNinno, C. Eller and J. B. Etienne, J. Org. Chem., 2001, 66, 6988;
78. (c) Y.-G. Suh, D.-Y. Shin, J.-K. Jung and S.-H. Kim, Chem. Commun., 2002, 1064;
79. (d) Y.-G. Suh, S.-H. Kim, J.-K. Jung and D.-Y. Shin, Tetrahedron Letts., 2002, 43, 3165;
80. (e) Similar 1'-hydroxyoxazolidinones (tetrahedral carbinols) have been reported by Evans el al. upon reduction of N-acyl pyrroles; see: D. A. Evans, G. Borg and K. A. Scheidt, Angew. Chem., Int. Ed., 2002, 41, 3188;
81. (f) This observation led to the use of pyrrole as a protecting group for aldehydes: D. J. Dixon, M. S. Scott and C. A. Luckhurst, Synlett. 2003, 2317.
82. The absolute configuration at C(1′) within oxazolidinones 9 and 10 was assigned by analogy to that proven unambiguously by X-ray crystallographic analysis for DIBAL reduction of a related substrate. See ref. 19.
83. (a) S. Masamune, W. Choy, J. S. Petersen and L. R. Sita, Angew. Chem., Int. Ed. Engl., 1985, 24, 1;
84. (b) For a recent review on the use of double diastereselective reactions in synthesis, see: O. I. Kolodiazhnyi, Tetrahedron, 2003, 59, 5953.
85. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
86. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
87. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
88. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
89. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
90. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
91. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
92. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
93. For other examples of double stereodifferentiating aldol reactions, see: (a) D. J. Gustin, M. S. Van Nieuwenhze and W. R. Roush, Tetrahedron Lett., 1995, 36, 3443; (b) S. Sano, X.-K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro and Y. Nagao, Tetrahedron Lett., 1995, 36, 4104; (c) E. J. Corey, W. Li and G. A. Reichard, J. Am. Chem. Soc., 1998, 120, 2330; (d) D. A. Evans, M. J. Dart, J. L. Duffy and D. L. Rieger, J. Am. Chem. Soc., 1995, 117, 9073; (e) D. A. Evans, P. J. Coleman and B. Cote, J. Org. Chem., 1997, 62, 788; (f) G. J. Bodwell, S. G. Davies and A. M. Mortlock, Tetrahedron, 1991. 48, 10077; (g) P. R. Beckett, S. G. Davies and A. M. Mortlock, Tetrahedron: Asymmetry, 1992, 3, 123; (h) A. N. Hulme and C. H. Montgomery, Tetrahedron Lett., 2003, 44, 7649; (i) J. L. Vicario, M. Rodriguez, D. Badia, L. Carrillo and E. Reyes, Org. Lett., 2004, 6, 3171.
94. (a) A. B. Smith III and G. R. Ott, J. Am. Chem. Soc., 1996, 118, 13095;
95. (b) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, R. C. Reichert and B. A. Salvatore, J. Am. Chem. Soc., 1995, 117, 12017.
96. D-Galactose 97%, Aldrich Chemical Company, £11.60 (100 g).
97. D-Fucose 96%, Aldrich Chemical Company, £34.50 (1 g).
98. M. B. Perry and V. Daoust, Can. J. Chem., 1973, 51, 3039.
99. A. Datta Gupta, R. Singh and V. K. Singh, Synlett, 1996, 69.
100. A. S. Kende, K. Liu, I. Kaldor, G. Dorey and K. Koch, J. Am. Chem. Soc., 1995, 117, 8258.
101. V. Bon and J. Vilarrasa, Tetrahedron Lett., 1990, 31, 567.
102. N. S. Wilson and B. A. Keay, J. Org. Chem, 1996, 61, 2918.
103. A. R. Vaino and W. A. Szarek, Chem. Commun., 1996, 2351.
104. L-Idose 95%, Sigma, £22.50 (10 mg).
105. α-D-(+)-Talose 97%, Aldrich Chemical Company, £12.70 (25 mg).
106. J. Defaye and A. Gadelle, Carbohydr. Res., 1984, 126, 165.
107. (a) P. A. Gent, R. Gigg and R. Conant, J. Chem. Soc., Perkin Trans. 1, 1972, 12, 1535;
108. (b) M. A. Nashed and L. Anderson, Carbohydr. Res., 1976, 511, 65;
109. (c) M. A. Nashed and L. Anderson, Carbohydr. Res., 1977, 562, 419.
110. 2,4-Bis(O-benzyl)-α-L-fucopyranose: M. Dejter-Juszynski and H. M. Flowers, Carbohydr. Res., 1973, 28, 61.
111. α-p and β-p refer to α-pyranose and β-pyranose species; α-f and β-f refer to α-furanose and β-furanose species.
112. Y. Tsuda, T. Nunozawa and K. Yoshimoto, Chem. Pharm. Bull., 1980, 28, 3223.