L-Proline catalyzed asymmetric aldol reactions of protected hydroxyacetone

New Journal of Chemistry

Volumn 27, Issue 8, 2003, Pages 1159-1160

  Liu, Huawei ^a   Peng, Lizeng ^a   Zhang, Tao ^a   Li, Yulin ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALDEHYDE; AMINO ACID; PROLINE;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0041326565     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b304019b     Document Type: Article

References (26)

1. (a) T. D. Machajewski and C. H. Wong, Angew. Chem., Int. Ed., 2000, 39, 1352;
2. (b) H. Gröger, E. M. Vogl and M. Shibasaki, Chem.-Eur. J., 1998, 4, 1137;
3. (c) S. G. Nelson, Tetrahedron: Asymmetry, 1998, 9, 357.
4. (a) T. Mukaiyama and S. Kobayashi, in Stereocontrolled Organic Synthesis, ed. B. M. Trost, Blackwell, London, 1994, p. 34;
5. (b) S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297;
6. (c) T. Mukaiyama, H. Uchiro, I. Shiina and S. Kobayashi, Chem. Lett., 1990, 1019;
7. (d) S. Kobayashi and M. Horibe, Chem.-Eur. J., 1997, 3, 1472;
8. (e) T. Mukaiyama, I. Shiina, H. Uchiro and S. Kobayashi, Bull. Chem. Soc. Jpn., 1994, 67, 1708.
9. (a) Y. M. A. Yamada and M. Shibasaki, Angew. Chem., Int. Ed., 1997, 36, 1871;
10. (b) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 2169;
11. (c) N. Yoshikawa and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 2466;
12. (d) N. Yoshikawa and M. Shibasaki, J. Am. Chem. Soc., 1999, 121, 4168;
13. (e) Y. M. A. Yamada and M. Shibasaki, Tetrahedron Lett., 1998, 39, 5561.
14. (a) B. M. Trost and H. Ito, J. Am. Chem. Soc., 2001, 123, 3367;
15. (b) B. M. Trost and H. Ito, J. Am. Chem. Soc., 2000, 122, 12003.
16. (a) B. List, P. Pojarliev, W. T. Biller and H. J. Martin, J. Am. Chem. Soc., 2002, 124, 827;
17. (b) B. List, R. A. Lerner and C. F. Barbas III, J. Am. Chem. Soc., 2000, 122, 2395;
18. (c) W. Notz and B. List, J. Am. Chem. Soc., 2000, 122, 7386;
19. (d) B. List, P. Pojarliev and C. Castello, Org. Lett., 2001, 3, 573;
20. (e) B. List, Tetrahedron, 2002, 58, 10 450;
21. (f) B. List, Synlett., 2001, 11, 1675.
22. For reviews and highlights of the proline catalyzed asymmetric direct aldol reaction in various contexts, see: (a) H. Gröger and J. Wilken, Angew. Chem., Int. Ed., 2001, 40, 529; (b) C. Palomo, M. Oiarbide and J. M. Garcia, Chem.-Eur. J., 2001, 8, 37; (c) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595; (d) M. Movassaghi and E. N. Jacobsen, Science, 2002, 298, 1904.
23. For reviews and highlights of the proline catalyzed asymmetric direct aldol reaction in various contexts, see: (a) H. Gröger and J. Wilken, Angew. Chem., Int. Ed., 2001, 40, 529; (b) C. Palomo, M. Oiarbide and J. M. Garcia, Chem.-Eur. J., 2001, 8, 37; (c) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595; (d) M. Movassaghi and E. N. Jacobsen, Science, 2002, 298, 1904.
24. For reviews and highlights of the proline catalyzed asymmetric direct aldol reaction in various contexts, see: (a) H. Gröger and J. Wilken, Angew. Chem., Int. Ed., 2001, 40, 529; (b) C. Palomo, M. Oiarbide and J. M. Garcia, Chem.-Eur. J., 2001, 8, 37; (c) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595; (d) M. Movassaghi and E. N. Jacobsen, Science, 2002, 298, 1904.
25. For reviews and highlights of the proline catalyzed asymmetric direct aldol reaction in various contexts, see: (a) H. Gröger and J. Wilken, Angew. Chem., Int. Ed., 2001, 40, 529; (b) C. Palomo, M. Oiarbide and J. M. Garcia, Chem.-Eur. J., 2001, 8, 37; (c) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595; (d) M. Movassaghi and E. N. Jacobsen, Science, 2002, 298, 1904.
26. The phenomenon that the regioisomeric product was the primary aldol product in the L-proline catalyzed aldol reaction was not reported in previous papers.