Organocatalytic asymmetric assembly reactions: One-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1685-1688

  Chowdari, Naidu S ^a   Ramachary, D B ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOALCOHOL; DICARBOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; PROLINE; SOLVENT; DICARBOXYLIC ACID; HETEROCYCLIC COMPOUND; KETONE;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENZYME MECHANISM; OPTICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM;

ALDEHYDES; AMINO ALCOHOLS; AZA COMPOUNDS; CATALYSIS; DICARBOXYLIC ACIDS; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROLINE; SOLVENTS; STEREOISOMERISM;

EID: 0042655108     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034333n     Document Type: Article

References (31)

1. Khosla, C. J. Org. Chem. 2000, 65, 8129.
2. Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
3. (a) Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500.
4. (b) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828.
5. (c) Yamasaki, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 1256.
6. (d) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 4609.
7. (e) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620.
8. (f) Du, H.; Ding, K. Org. Lett. 2003, 5, 1091.
9. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
10. (b) Saktihvel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260.
11. (c) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301.
12. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
13. (e) Bogevig, A.; Juhl, K., Kumaragurubaran, N.; Jorgensen, K. A. Chem. Commun. 2002, 620.
14. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479.
15. (a) Notz, W.; Sakthivel, K.; Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199.
16. (b) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
17. (c) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
18. (d) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
19. (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441.
20. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737.
21. (c) Enders, D.; Seki, A. Synlett 2002, 26.
22. (a) Thayumanavan, R., Ramachary, D. B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 3817.
23. (b) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 6743.
24. (a) Bogevig, A.; Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
25. (b) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
26. (c) List, F. J. Am. Chem. Soc. 2002, 124, 5656.
27. Chowdari, N. S.; Ramachary, D. B.; Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591.
28. (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
29. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
30. Juraszyk, H.; Schmitges, C. J.; Minck, K. O.; Raddatz, P. (Merck Patent G.m.b.H., Germany). Eur. Pat. Appl. EP 490259 A2, 1992.
31. 4), concentrated, and purified by flash column chromatography (silica gel, mixtures of hexanes/ethyl acetate) to afford the desired amino alcohol as a white solid as a mixture of diastereomers.