Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: Step one in a two-step synthesis of carbohydrates

Angewandte Chemie - International Edition

Volumn 43, Issue 16, 2004, Pages 2152-2154

  Northrup, Alan B ^a   Mangion, Ian K ^a   Hettche, Frank ^a   MacMillan, David W C ^a  

^a California Institute of Technology   (United States)

Author keywords

Aldehydes; Aldol reaction; Carbohydrates; Enantioselectivity; Homogeneous catalysis

Indexed keywords

CARBOHYDRATES; CATALYSTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYTIC DIRECT ALDOL REACTIONS;

ALDEHYDES;

ALDEHYDE DERIVATIVE; CARBOHYDRATE; ORGANIC COMPOUND; POLYOL;

ALDOL REACTION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 3242806955     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453716     Document Type: Article

References (31)

1. a) Glycoscience: Chemistry and Chemical Biology I-III (Eds.: B. Fraser-Reid, K. Tatsuta, J. Thiem), Springer, 2001;
2. b) Glycochemistry: Principles, Synthesis, and Applications (Eds.: P. Wang, C. Bertozzi), Marcel Dekker, 2001.
3. While the term carbohydrate can be applied to many hydrated forms of carbon structure, we employ this terminology in the more commonly used and specific sense to describe hexose architecture.
4. a) K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465;
5. b) K. C. Nicolaou, H. J. Mitchel, Angew. Chem. 2001, 113, 1624; Angew. Chem. Int. Ed. 2801, 40, 1576.
6. b) K. C. Nicolaou, H. J. Mitchel, Angew. Chem. 2001, 113, 1624; Angew. Chem. Int. Ed. 2001, 40, 1576.
7. For some reviews of the aldol reaction, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 10, 1595;
8. b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352;
9. b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352;
10. c) R. Mahrwald, Chem. Rev. 1999, 99, 1095;
11. D. A. Evans, J. V. Nelson, T. Taber in Topics in Stereochemistry, Vol. 13, Wiley, 1982, p. 1.
12. For recent examples of aldol reactions in the syntheses of carbohydrates, see: a) D. A. Evans, E. Hu, J. S. Tedrow, Org. Lett. 2001, 3, 3133;
13. b) S. G. Davies, R. L. Nicholson, A. D. Smith, Synlett 2002, 10, 1637;
14. c) M. P. Sibi, J. Lu, J. Edwards, J. Org. Chem. 1997, 62, 5864;
15. d) for a review of aldolase enzymes in carbohydrate synthesis, see: S. Takayama, G. J. McGarvey, C.-H. Wong, Chem. Soc. Rev. 1997, 26, 407.
16. A two-step carbohydrate synthesis has recently been accomplished in our laboratories. Details of this work will be published at a later date.
17. For examples of enamine-catalyzed aldol reactions between α-oxyketones and -aldehydes, see: a) W. Noltz, B. List, J. Am. Chem. Soc. 2000, 122, 7386;
18. b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260.
19. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798.
20. For uses of erythrose in synthesis, see: a) W. H. Pearson, E. J. Hembre, J. Org. Chem. 1996, 61, 7217;
21. b) M. Ruiz, V. Ojea, J. M. Quintela, Synlett 1999, 2, 204;
22. c) J. G. Buchanan, A. R. Edgar, B. D. Hewitt, J. Chem. Soc. Perkin Trans. 1 1987, 2371.
23. A proline-catalyzed trimerization of propionaldehyde to form nearly racemic tetrahydropyrans in good diastereoselectivities with low yields has been reported: N. S. Chowdari, D. B. Ramachary, A. Cordova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591.
24. For examples of metal-mediated direct aldol reactions see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
25. For examples of metal-mediated direct aldol reactions see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
26. b) N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Oshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466;
27. c) N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Oshima, M. Shibasaki, Org. Lett. 2001, 3, 1539;
28. d) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003;
29. e) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497;
30. f) D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392;
31. g) G. Lalic, A. Aloise, M. Shair, J. Am. Chem. Soc. 2003, 125, 2852.