A fast and efficient deprotection of aldehydes from acylals using a Wells-Dawson heteropolyacid catalyst (H6P2W 18O62 · 24H2O)

Synthetic Communications

Volumn 34, Issue 21, 2004, Pages 3909-3914

  Romanelli, G P ^a   Autino, J C ^a   Baronetti, G ^b   Thomas, H J ^a  

^a FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

1,1 Diacetate; Acylal; Aldehyde; Heteropolyacid; Protecting group; Wells Dawson catalyst

Indexed keywords

ACETIC ACID DERIVATIVE; ACID; ALDEHYDE 1,1 DIACETATE DERIVATIVE; ALDEHYDE DERIVATIVE; NITROBENZALDEHYDE 1,1 DIACETATE DERIVATIVE; SILICON DIOXIDE; SOLVENT; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DEPROTECTION REACTION; EXTRACTION; REACTION ANALYSIS; REACTION TIME; REPRODUCIBILITY; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE;

EID: 7644238909     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200034783     Document Type: Article

References (15)

1. Greene, T.W.; Wuts, P.G.M. Protection for the carbonyl group. In Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley: New York, 1991; 184.
2. 2O). Tetrahedron Lett. 2003, 44, 1301-1303.
3. Banks, R.E.; Miller, J.A.; Nunn, J.M.; Stanley, P.; Weakley, T.J.R.; Ullah, Z. Diels-Alder route to potential trichothecene precursors. J. Chem. Soc. Perkin Trans, 1 1981, 1096-1102.
4. (a) Lieberman, S.V.; Connor, R. p-Nitrobenzaldehyde. Org. Synth. 1951, 2, 441-443;
5. (b) Tsang, S.M.; Wood, E.H.; Johnson, J.R. o-Nitrobenzaldehyde. Org. Synth. 1955, 3, 641-643.
6. Jin, T-.S.; Ma, Y-.R.; Zhang, Z-.H.; Li, T.-S. An efficient and facile procedure for the deprotection of 1,1-diacetates catalysed by expansive graphite. Synth. Commun. 1997, 27, 3379-3383 (and references cited therein).
7. Mohammadpoor-Baltork, I.; Aliyan, H. Bismuth (III) chloride; an efficient and selective catalyst for deprotection of 1,1-diacetates. Synth. Commun. 1999, 29, 2741-2746.
8. Ballini, R.; Bordoni, M.; Bossica, G.; Maggi, R.; Sartori, G. Solvent free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst. Tetrahedron Lett. 1998, 39, 7587-7590.
9. 3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals); chemoselective protection of aldehydes in presence of ketones. Synlett 1998, 849-850.
10. 4. Synth. Commun. 2001, 31, 1091-1095.
11. Baronetti, G.; Briand, L.; Sedran, U.; Thomas, H. Heteropolyacid-based catalysis. Dawson acid for MTBE synthesis in gas phase. Appl. Catal. A 1998, 172, 265-272.
12. 9-, as a uniquely active nickel-based catalyst for the activation of hydrogen peroxide and the epoxidation of alkenes and alkenols. Chem. Europ. J. 2000, 6, 3722-3728.
13. Romanelli, G.P.; Autino, J.C.; Baronetti, G.; Thomas, H. Efficient deprotection of phenol methoxymethyl ethers using a solid acid catalyst with Wells-Dawson structure. Molecules 2001, 6, 1006-1011.
14. Romanelli, G.P.; Baronetti, G.; Thomas, H.; Autino, J.C. Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure. Tetrahedron Lett. 2002, 43, 7589-7591.
15. Kengaku, T.; Matsumoto, Y.; Na, K.; Misono, M. Michael addition in the pseudoliquid phase of heteropoly compounds. J. Mol. Catal. 1998, 134, 237-242.