Solvent-free chemoselective synthesis of 1,1-diacetates catalyzed by Cu(NO3)2·3H2O

Synthetic Communications

Volumn 37, Issue 7, 2007, Pages 1121-1126

  Heravi, Majid M ^a   Bakhtiari, Khadijeh ^a   Tehrani, Maryam H ^a   Oskooie, Hossein A ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

1,1 diacetates; Acylals; Aldehydes; Chemoselective; Cu(NO3)2 3H2O

Indexed keywords

ACETOACETIC ACID DERIVATIVE; COPPER DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 34147117602     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701198906     Document Type: Article

References (26)

1. Toda, F.; Tanaka, K. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025.
2. Dolman, S. J.; Satterly, E. S.; Hoveyda, A. H.; Schrock, R. R. Efficient catalytic enantioselective synthesis of unsaturated amines: Preparation of small- and medium-ring cyclic amines through Mo-catalyzed asymmetric ring-closing metathesis in the absence of solvent. J. Am. Chem. Soc. 2002, 124, 6991.
3. Balema, V. P.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. Mechanically induced solid-state generation of phosphorus ylides and the solvent-free Wittig reaction. J. Am. Chem. Soc. 2002, 124, 6244.
4. Green, T. W.; Wuts, P. G. M. Protecting Groups in Organic Chemistry, 3rd ed.; Wiley and Sons: New York, 1999.
5. Chakaraborti, A. K.; Thilagavathi, R.; Kumar, R. Copper (II) tetrafluoroborate-catalyzed formation of aldehyde-1,1-diacetates. Synthesis. 2004, 831.
6. 2O). Tetrahedron Lett. 2003, 44, 1301.
7. Karimi, B.; Maleki, J. Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions. J. Org. Chem. 2003, 68, 4951.
8. Heerden, F. R.; Huyser, J. J.; Williams, D. B. G.; Holzapfel, C. W. Palladium-catalysed substitution reactions of geminal allylic diacetates. Tetrahedron Lett. 1998, 39, 5281.
9. Trost, B. M.; Lee, C. Gem-Diacetates as carbonyl surrogates for asymmetric synthesis: Total syntheses of sphingofungins E and F. J. Am. Chem. Soc. 2001, 123, 12191.
10. Frick, J. G., Jr.; Harper, R. J., Jr. Acetals as cross linking reagents for cotton. J. Appl. Polym. 1984, 29, 1433.
11. 3H. Green Chem. 2002, 4, 255.
12. Aggen, D. H.; Arnold, J. N.; Hayes, P. D.; Smoter, N. J.; Mohan, R. S. Bismuth compounds in organic synthesis: Bismuth nitrate catalyzed chemoselective synthesis of acylals from aromatic aldehydes. Tetrahedron 2004, 60, 3675.
13. 4- catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage. Tetrahedron 2003, 59, 9571, and references cited therein.
14. 2 under microwave irradiation. Synth. Commun. 2002, 32, 3469.
15. Reddy, A. V.; Ravinder, K.; Reddy, V. L. N.; Ravinkanth, V.; Yenkateswarlu, Y. Amberlyst-15-catalyzed efficient synthesis of 1,1-diacetates from aldehydes. Synth Commun. 2003, 33, 1531.
16. 40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diacetates (acylals) under solvent-free conditions. Tetrahedron Lett. 2003, 44, 3951.
17. 4: A catalyst for the chemoselective preparation of 1,1-diacetates from aldehydes under solvent-free conditions. Green Chem. 2005, 7, 867.
18. Heravi, M. M.; Taheri, S.; Bakhtiari, K.; Oskooie, H. A. Cupric sulfate pentahydrate: A mild and efficient catalyst for the chemoselective synthesis of 1,1-diacetates from aldehydes in a solvent-free system. Monatsh. Chem. 2006, in press.
19. Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F. An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid. Catal. Commun. 2006, 7, 499.
20. 40): A novel and efficient recyclable catalyst for synthesis of 1,1-diacetates from aromatic aldehydes in solvent-free system and their deprotection. Synth. Commun. 2006, 36, 3109.
21. Freeman, I.; Karcherski, E. M. Preparation and spectral properties of benzylidene diacetates. J. Chem. Eng. Data. 1977, 22, 355.
22. Jin, T.-S.; Du, G.-Y.; Li, T.-S. An efficient and convenient procedure for the synthesis of 1,1-diacetates of aldehydes catalyzed by anhydrous ferrous sulfate. Ind. J. Chem. 1998, 37 (B), 939.
23. Negron, G. E.; Palacios, L. N.; Angeles, D.; Lomas, L.; Gavino, R. A mild and efficient method for the chemoselective synthesis of acylals from aromatic aldehydes and their deprotections catalyzed by sulfated zirconia. J. Braz. Chem. Soc. 2005, 16 (3A), 490.
24. Zhang, Z. H.; Li, T. S.; Fu, C. G. Montmorillonite clay catalysis, part 4: An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes. J. Chem. Res. Synop. 1997, 174.
25. 42-solid superacid. J. Chem. Res. Synop. 2000, 96.
26. Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyksha, S. R.; Pinnick, H. W. Protecting groups in organic synthesis, part 8: Conversion of aldehydes into geminal diacetates. J. Org. Chem. 1983, 48, 1765.