Synthesis of azasugars through a proline-catalyzed reaction

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 6258-6261

  Calderón, Félix ^a   Doyagüez, Elisa G ^a   Fernández Mayoralas, Alfonso ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; ANTI-ALDOL PRODUCTS; ENANTIOMERS;

CATALYSIS; CONDENSATION; NITROGEN COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

SUGARS;

AZASUGAR DERIVATIVE; DIETHYLTARTRATE; PROLINE; SUGAR; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; AZA COMPOUNDS; CARBOHYDRATES; CATALYSIS; HYDROGEN; MOLECULAR STRUCTURE; PROLINE;

EID: 33746883942     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060568b     Document Type: Article

References (17)

1. (a) Kazmaier, U. Angew. Chem., Int. Ed. 2005, 44, 2186-2188.
2. (b) Enders, D.; Grondal, C. Angew. Chem., Int. Ed. 2005, 44, 1210-1212.
3. (c) Cordova, A.; Engqvist, M.; Ibrahem, I.; Casas, J.; Sundén, H. Chem. Commun. 2005, 2047-2049.
4. (d) Northrup, A. B.; MacMillan, W. C.; Science 2004, 305, 1752-1755.
5. (d) Suri, J. T.; Mitsumori, S.; Albertshofer, K.; Tanaka, F.; Barbas, C. F., III. J. Org. Chem. 2006, 71, 3822-3828.
6. Calderón F.; Fernández R.; Sánchez, F.; Fernández-Mayoralas, A. Adv. Synth. Catal. 2005, 347, 1395-1403
7. Bastida, A.; Fernández-Mayoralas, A.; Gómez, R.; Iradier, F.; Carretero, J. C.; García-Junceda, E. Chem.-Eur. J. 2001, 7, 2390-2397.
8. (b) Carpintero, M.; Bastida, A.; García-Junceda, E.; Jiménez-Barbero, J.; Fernández-Mayoralas, A. Eur. J. Org. Chem. 2001, 4127-4135.
9. (c) Calderón, F.; Carpintero, M.; García-Junceda, E.; Fernández-Mayoralas, A.; Bastida, A. Lett. Org. Chem. 2005, 2, 247-254.
10. Stutz, A. E. In Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Wiley-VCH: Weinheim, Germany, 1999.
11. Pearson, M. S. M.; Mathé-Allainmat, M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem. 2005, 2159-2191.
12. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091.
13. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041-3043.
14. 1H NMR spectra of the corresponding diesters (R)- and (S)-methoxyphenylacetic acid (see Supporting Information). The assigned configuration data were reconfirmed in the final cyclized compounds.
15. Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479.
16. Asano, N.; Nishida, M.; Kato, A.; Kizu, H.; Matsui, K.; Shimada, Y.; Itoh, T.; Baba, M.; Watson, A. A.; Nash, R. J.; de Q. Lilley, P. M.; Watkin, D. J.; G. Fleet, G. W. J. J. Med. Chem. 1998, 41, 2565-2571.
17. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091.