Synthesis of 1,1-diacetates using a new combined catalytic system: Copper p-toluenesulfonate/HOAc

Synthetic Communications

Volumn 38, Issue 6, 2008, Pages 961-966

  Wang, Min ^a   Song, Zhiguo ^a   Gong, Hong ^b   Jiang, Heng ^b  

^a BOHAI UNIVERSITY   (China)

^b LIAONING SHIHUA UNIVERSITY   (China)

Author keywords

Acetic acid; Copper p toluenesulfonate; Diacetates

Indexed keywords

ACETOACETIC ACID; ALDEHYDE; COPPER; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; SYNTHESIS;

EID: 39749168298     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701845720     Document Type: Article

References (13)

1. Wang, M.; Wang, Z. C.; Sun, Z. L.; Jiang, H. Reaction-controlled recovery of the copper (II) methanesulfonate catalyst for esterification. React. Kinet. Catal. Lett. 2005, 84, 223-228.
2. Wang, M.; Wang, Z. C.; Sun, Z. L.; Jiang, H. Synthesis and characterization of transition metal methanesulfonates and their catalytic behavior in Biginelli reactions. Transition Met. Chem. (London) 2005, 30, 792-796.
3. Zhang, L. H.; Jiang, H.; Gong, H.; Sun, Z. L. Characteristics of thermal decomposition products of rare earth, alkali earth metal and transition metal p-toluenesulfonates. J. Therm. Anal. Calorim. 2005, 79, 731-735.
4. Wang, M.; Gong, H.; Jiang, H.; Wang, Z. C. Acetic acid-assisted copper methanesulfonate catalyst for chemoselective conversion of aldehydes to acylals. Synth. Commun. 2006, 36, 1953-1960.
5. 3H. Green Chem. 2002, 4, 255-256.
6. Freeman, F.; Karchefski, E. M. Preparation and spectral properties of benzylidene diacetates. J. Chem. Eng. Data. 1977, 22, 355-357.
7. Pereira, C.; Gigante, B.; Marcelo-Curto, M. J.; Carreyre, H.; Pérot, G.; Guisnet, M. Diacetates from aldehydes in the presence of zeolites. Synthesis 1995, 1077-1078.
8. Yadav, J. S.; Reddy, B. V. S.; Srinivas, C. Indium trichloride-catalyzed chemoselective conversion of aldehydes to gem-diacetates. Synth. Commun. 2002, 32, 2169-2174.
9. Eshghi, H.; Gordi, Z. Phosphorus pentoxide-montmorillonite K-10 as catalyst for the preparartion of 1,1-diacetates under solvent-free conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1341-1346.
10. 3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions. Tetrahedron Lett. 2007, 48, 2881-2884.
11. Ciufolini, M. A.; Deaton, M. V.; Zhu, S. R.; Chen, M. Y. A remarkable ene-like reaction: Development and synthetic applications. Tetrahedron. 1997, 53, 16299-16312.
12. Mouhtady, O.; Gaspard-Houghmane, H.; Roques, N.; Roux, C. L. Metal triflates-methanesulfonic acid as new catalytic systems: Application to the Fries rearrangement. Tetrahedron Lett. 2003, 44, 6379-6382.
13. Ishihara, K.; Yamamoto, H. Brønsted acid-assisted chiral Lewis acid (BLA) catalysis for asymmetric Diels-Alder reaction. J. Am. Chem. Soc. 1994, 116, 1561-1562.