Asymmetric mukaiyama-aldol reaction in aqueous media promoted by zinc-based chiral lewis acids

Advanced Synthesis and Catalysis

Volumn 347, Issue 4, 2005, Pages 521-525

  Mlynarski, Jacek ^a   Jankowska, Joanna ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Asymmetric catalysis; Homogeneous catalysis; Lewis acids; Mukaiyama aldol reaction; N ligands; Water

Indexed keywords

ACETOPHENONE; ALDEHYDE DERIVATIVE; LEWIS ACID; PROPIOPHENONE DERIVATIVE; ZINC;

AQUEOUS SOLUTION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; STEREOCHEMISTRY;

EID: 17144425732     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404314     Document Type: Article

References (23)

1. a) T. D. Machajewski, Ch.-H. Wong, Angew. Chem. Int. Ed. 2000, 39, 1352-1374;
2. b) C. Palomo, M. Oiarbide, J. M. Garcia, Chem. Soc. Rev. 2004, 33, 65-75.
3. a) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
4. b) D. Sinou, Adv. Synth. Catal. 2002, 344, 221-237;
5. c) K. Manabe, S. Kobayashi, Chem. Eur. J. 2002, 8, 4095-4101;
6. d) S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209-217.
7. a) F. Fringuelli, O. Piermatti, F. Pizzo, in: Organic Synthesis in Water, (Ed.: P. A. Grieco), Blackie Academic & Professional, London, 1998, pp. 250-261;
8. b) S. Kobayashi, in: Organic Synthesis in Water, (Ed.: P. A. Grieco), Blackie Academic & Professional, London, 1998, pp. 262-302.
9. S. Kobayashi, S. Nagayama, T. Busujima, Tetrahedron, 1999, 55, 8739-8746.
10. S. Nagayama, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 11531-11532.
11. H.-J. Li. H.-Y. Tian, Y.-J. Chen, D. Wang, Ch.-J. Li, Chem. Commun., 2002, 2994-2995.
12. T. Hamada, K. Manabe, S. Ishikawa, S. Nagayama, M. Shiro, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 2989-2996.
13. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236-12237.
14. a) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169-2178;
15. b) B. M. Trost. H. Ito, J. Am. Chem. Soc. 2000, 122, 12003-12004;
16. c) B. M. Trost. H. Ito, E. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367-3368;
17. d) B. M. Trost. E. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497-2500.
18. a) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641;
19. b) T. Hamada, K. Manabe, S. Kobayashi, Angew. Chem. In. Ed. 2003, 42, 3927-3930;
20. c) T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7768-7769.
21. G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev., 2003, 103, 3119-3154.
22. [7]
23. The absolute configuration of the alcohol 13a was determined by comparison of optical rotation with literature data: S. H. Mashraqui, R. M. Kellogg, J. Org. Chem. 1984, 49, 2513-2516.