A catalytic aldol reaction and condensation through in situ boron "ate" complex enolate generation in water

Angewandte Chemie - International Edition

Volumn 47, Issue 4, 2008, Pages 768-770

  Aelvoet, Karel ^a   Batsanov, Andrei S ^a   Blatch, Alexandrea J ^a   Grosjean, Christophe ^a   Patrick, Leonard G F ^a   Smethurst, Christian A ^b   Whiting, Andrew ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Aldol reaction; Bifunctional catalysts; Boron; Homogeneous catalysis; Selectivity

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; CONDENSATION; WATER;

ALDOL CONDENSATION; ALDOL REACTION; BIFUNCTIONAL CATALYSTS; HOMOGENEOUS CATALYSIS; IMIDAZOLE FUNCTION;

BORON;

ALDEHYDE; BORON DERIVATIVE; KETONE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; BORON COMPOUNDS; CATALYSIS; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM; WATER;

EID: 38349016812     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704293     Document Type: Article

References (38)

1. U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772.
2. a) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430;
3. Angew. Chem. Int. Ed. 2000, 39, 1352-1374;
4. b) T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221;
5. c) S. Nagayama, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 11531-11532;
6. d) S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236-12237;
7. e) C. M. Cinquini, F. Cozzi, G. Celentano, Org. Biomol. Chem. 2004, 2, 2401-3407.
8. Y. Mori, J. Kobayashi, K. Manabe, S. Kobayashi, Tetrahedron 2002, 58, 8263-8268.
9. Y. Mori, K. Manabe, S. Kobayashi, Angew. Chem. 2001, 113, 2897-2900;
10. Angew. Chem. Int. Ed. Engl. 2001, 40, 2815-2818.
11. a) R. L. Letsinger, S. H. Dandegaonker, J. Am. Chem. Soc. 1959, 81, 498-501;
12. b) R. L. Letsinger, A. J. Wysocki, J. Org. Chem. 1963, 28, 3199-3202.
13. a) R. L. Letsinger, D. B. MacLean, J. Am. Chem. Soc. 1963, 85, 2230-2236;
14. b) R. L. Letsinger, J. D. Morrison, J. Am. Chem. Soc. 1963, 85, 2227-2229.
15. a) R. L. Giles, J. A. K. Howard, L. G. F. Patrick, M. R. Probert, G. E. Smith, A. Whiting, J. Organomet. Chem. 2003, 680, 257-262;
16. b) S. W. Coghlan, R. L. Giles, J. A. K. Howard, M. R. Probert, G. E. Smith, A. Whiting, J. Organomet. Chem. 2005, 690, 4784-4793;
17. c) K. Arnold, B. Davies, R. L. Giles, C. Grosjean, G. E. Smith, A. Whiting, Adv. Synth. Catal. 2006, 348, 813-820;
18. d) A. J. Blatch, O. V. Chetina, J. A. K. Howard, L. G. F. Patrick, C. A. Smethurst, A. Whiting, Org. Biomol. Chem. 2006, 4, 3297-3302;
19. e) D. Hérault, K. Aelvoet, A. J. Blatch, A. Al-Majid, C. A. Smethurst, A. Whiting, J. Org. Chem. 2007, 72, 71-75.
20. The data analysis was done using Scientist version 2.01, Micro-Math Research, Saint Louis, Missouri, USA.
21. T. D. Machajewski, C. H. Wong, Angew. Chem. 2000, 112, 1406-1430;
22. Angew. Chem. Int. Ed. 2000, 39, 1352-1374.
23. a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
24. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387;
25. c) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
26. d) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954;
27. e) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575;
28. f) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798-6799;
29. g) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688;
30. h) T. Darbre, M. Machuqueiro, Chem. Commun. 2003, 1090-1091;
31. i) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
32. j)T. J. Dickerson, Janda, J. Am. Chem. Soc. 2002, 124, 3220-3221;
33. k) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689;
34. Angew. Chem. Int. Ed. 2003, 42, 661-665.
35. 1,3,2-Dioxaboroles are known from α-hydroxy-ketone enolates, see a) R. L. Letsinger, S. B. Hamilton, J. Org. Chem. 1960, 25, 592-595;
36. b) G. Smolinsky, J. Org. Chem. 1961, 26, 4915-4917.
37. a) J. Mulzer, G. Brüntrup, J. Finke, M. Zippel, J. Am. Chem. Soc. 1979, 101, 7723-7725;
38. b) S. Murata, M. Suzuki, R. Noyori, J. Am. Chem. Soc. 1980, 102, 3248-3249.