Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1527-1530

  Yao, Wengang ^a   Wang, Jianbo ^a  

^a Peking University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; ZIRCONIUM DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; POLYMERIZATION;

EID: 0141786837     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0343257     Document Type: Article

References (23)

1. For recent reviews on the catalytic asymmetric aldol reaction, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol.3, Chapter 29.1. (c) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; p 493.
2. For recent reviews on the catalytic asymmetric aldol reaction, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol.3, Chapter 29.1. (c) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; p 493.
3. For recent reviews on the catalytic asymmetric aldol reaction, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 37. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol.3, Chapter 29.1. (c) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; p 493.
4. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
5. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
6. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
7. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
8. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
9. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
10. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
11. For reviews, see: (a) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989. (b) Alcaide, B.; Almemdros, P. Eur. J. Org. Chem. 2002, 1595. (c) List, B. Tetrahedron 2002, 58, 5573. (d) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187. For most recent reports, see: (e) Ooi, T.; Taniguchi, M.; Kemeda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (f) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc., 2002, 124, 6798. (g) Evans, D.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 392. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
12. Jiang, N.; Wang, J. Tetrahedron Lett. 2002, 43, 1285.
13. 4 and 1 equiv of (S)-4 gave the condensation product in 53% yield and 15% ee.
14. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180.
15. The Zr(IV) catalyst prepared with 1 equiv of (S)-4 gave lower enantioselectivity.
16. 3-CN gave the best results in terms of ee value.
17. The absolute configuration was determined by converting 3a into a known compound of ethyl 3-hydroxy-3-phenylpropionate and comparing the sign of optical rotation. See Supporting Information.
18. 2Et were removed with rotovap. The crude residue was purified with silica gel column (petroleum ether/acetone = 8:1).
19. 2 has been shown to efficiently bind to β-hydroxyl esters. See: Bouzide, A. Org. Lett. 2002, 4, 1347.
20. 4 is reported to catalyze intramolecular Michael-Aldol reaction; see: Attah-Poku, S. K.; Chau, F.; Yadav, V. K.; Fallis, A. G. J. Org. Chem. 1985, 50, 3418.
21. For comprehensive reviews on the chemistry of α-diazo carbonyl compounds, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 44, 1091.
22. For comprehensive reviews on the chemistry of α-diazo carbonyl compounds, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 44, 1091.
23. Desai, S. B.; Argade, N. P.; Ganesh, K. N. J. Org. Chem. 1996, 61, 6730.