Silica Phosphoric Acid: An Efficient and Recyclable Catalyst for the Solvent-Free Synthesis of Acylals and Their Deprotection in MeOH

REFERENCES

• Green , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis; , 3rd ed. ; John Wiley & Sons, Inc. : New York , 1999 .
   Google Scholar
• Kochhar , K. S. ; Bal , B. S. ; Deshpande , R. P. ; Rajadhyaksha , S. N. ; Pinnick , H. W. Protecting groups in organic synthesis, part 8: Conversion of aldehydes into geminal diacetates . J. Org. Chem. 1983 , 48 , 1765 – 1767 .
   Web of Science ®Google Scholar
• Snider , B. B. ; Amin , S. B. An improved synthesis of 1α,3β-dihydroxycholesta-5,7-diene . Synth. Commun. 1978 , 8 , 117 – 125 .
   Web of Science ®Google Scholar
• Sydnes , L. K. ; Sandberg , M. The chemistry of acylals, part I: The reactivity of acylals towards Grignard and organolithium reagents . Tetrahedron 1997 , 53 , 12679 – 12690 .
   Web of Science ®Google Scholar
• Heerden , F. R. ; Huyser , J. J. ; Williams , B. D. G. ; Holzapfel , C. W. Palladium-catalysed substitution reactions of geminal allylic diacetates . Tetrahedron Lett. 1998 , 39 , 5281 – 5284 .
   Web of Science ®Google Scholar
• Sandberg , M. ; Sydnes , L. K. The chemistry of acylals, part II: Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of a Lewis acid . Tetrahedron Lett. 1998 , 39 , 6361 – 6364 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Subba Reddy , B. V. ; Madhuri , C. ; Sabitha , G. Indium(III) chloride–catalyzed allylation of gem-diacetates: A facile synthesis of homoallyl acetates . Chem. Lett. 2001 , 30 , 18 – 19 .
   Google Scholar
• Trost , B. M. ; Lee , C. B. Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis, part I: Asymmetric addition of malonate nucleophiles . J. Am. Chem. Soc. 2001 , 123 , 3671 – 3686 .
   PubMedGoogle Scholar
• Trost , B. M. ; Lee , C. B. Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis, part II: Scope and applications . J. Am. Chem. Soc. 2001 , 123 , 3687 – 3696 .
   PubMedGoogle Scholar
• 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 – 12201 .
   PubMed Web of Science ®Google Scholar
• Tomita , M. ; Kikuchi , T. ; Bessho , K. ; Hori , T. ; Inubushi , Y. Studies on pilocereine and related compounds, III: Synthesis of 2,2′,3-trimethoxydiphenyl ether-4′,5- and 4′,6-dicarboxaldehyde . Chem. Pharm. Bull. 1963 , 11 , 1484 – 1490 .
   PubMedGoogle Scholar
• Marshall , J. A. ; Wuts , P. G. M. Stereoselective synthesis of racemic occidentalol and related cis-fused hexahydronaphthalenes from m-toluic acid. J. Org. Chem. 1977, 42, 1794–1798.
   Web of Science ®Google Scholar
• Michie , J. K. ; Miller , J. A. Phosphorus trichloride as catalyst in the preparation of 1,1-diacetates from aldehydes . Synthesis 1981 , 824 .
   Google Scholar
• Deka , N. ; Kalita , D. J. ; Borah , R. ; Sarma , J. C. Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes . J. Org. Chem. 1997 , 62 , 1563 – 1564 .
   Web of Science ®Google Scholar
• Agarwal , V. K. ; Fonquerna , S. ; Vennall , G. P. Sc(OTf)3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals): Chemoselective protection of aldehydes in presence of ketones . Synlett 1998 , 849 – 850 .
   Google Scholar
• Chandra , K. L. ; Saravanan , P. ; Singh , V. K. An efficient method for diacetylation of aldehydes . Synlett 2000 , 359 – 360 .
   Google Scholar
• Karimi , B. ; Seradj , H. ; Ebrahimian , R. G. Mild and efficient conversion of aldehydes to 1,1-diacetates catalyzed with N-bromosuccinimide (NBS) . Synlett 2000 , 623 – 624 .
   Web of Science ®Google Scholar
• Carrigan , M. D. ; Eash , K. J. ; Oswald , M. C. ; Mohan , R. S. An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate . Tetrahedron Lett. 2001 , 42 , 8133 – 8135 .
   Web of Science ®Google Scholar
• Wang , C. ; Li , M. A novel and efficient conversion of aldehydes to 1,1-diacetates catalyzed with FeCl3/SiO2 under microwave irradiation . Synth. Commun. 2002 , 32 , 3469 – 3473 .
   Web of Science ®Google Scholar
• Roy , S. C. ; Banerjee , B. A mild and efficient method for the chemoselective synthesis of acylals from aldehydes and their deprotections catalysed by ceric ammonium nitrate . Synlett 2002 , 1677 – 1678 .
   Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Venugopal , C. ; Ramalingam , T. LiBF4-mediated conversion of aldehydes to gem-diacetates . Synlett 2002 , 604 – 606 .
   Google Scholar
• Jin , T. S. ; Sun , G. ; Li , Y. W. ; Li , T. S. An efficient and convenient procedure for the preparation of 1,1-diacetates from aldehydes catalyzed by H2NSO3H . Green Chem. 2002 , 4 , 255 – 256 .
   Web of Science ®Google Scholar
• Satam , J. R. ; Jayaram , R. V. (NH4)3PW12O40 as an efficient and reusable catalyst for the synthesis and deprotection of 1,1-diacetates . Synth. Commun. 2008 , 38 , 595 – 602 .
   Web of Science ®Google Scholar
• Romanelli , G. P. ; Thomas , H. J. ; Baronetti , G. T. ; Autino , J. C. Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells–Dawson acid (H6P2W18O62 · 24H2O) . Tetrahedron Lett. 2003 , 44 , 1301 – 1303 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Nowrouzi , F. ; Amani , K. Aluminum dodecatungstophosphate (AlPW12O40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diacetates (acylals) under solvent-free conditions . Tetrahedron Lett. 2003 , 44 , 3951 – 3954 .
   Web of Science ®Google Scholar
• Ghosh , R. ; Maiti , S. ; Chakraborty , A. ; Halder , R. Indium triflate: A reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals . J. Mol. Catal. A 2004 , 215 , 49 – 53 .
   Google Scholar
• 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 – 3679 .
   Web of Science ®Google Scholar
• Kumar , P. ; Hegde , V. R. ; Kumar , T. P. An efficient synthesis of diacetates from aldehydes using β-zeolite . Tetrahedron Lett. 1995 , 36 , 601 – 602 .
   Web of Science ®Google Scholar
• Nagy , N. M. ; Jakab , M. A. ; Konya , J. ; Antus , S. Convenient preparation of 1,1-diacetates from aromatic aldehydes catalysed by zinc–montmorillonite . Appl. Clay. Sci. 2002 , 21 , 213 – 216 .
   Web of Science ®Google Scholar
• Hajipour , A. R. ; Zarei , A. ; Ruoho , A. E. P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 2881 – 2884 .
   Web of Science ®Google Scholar
• Zolfigol , M. A. ; Shirini , F. ; Zamani , K. ; Ghofrani , E. ; Ebrahimi , S. Silica phosphoric acid/NaNO2 as a novel heterogeneous system for the coupling of thiols to their corresponding disulfides. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2177–2182.
   Web of Science ®Google Scholar
• Khan , A. T. ; Choudhury , L. H. ; Ghosh , S. Silica-supported perchloric acid (HClO4-SiO2): A highly efficient and reusable catalyst for geminal diacylation of aldehydes under solvent-free conditions . J. Mol. Catal. A 2006 , 255 , 230 – 235 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Ramalingam , T. ; Srinivas , R. ; Reddy , B. V. S. ; Yadav , J. S. A mild and efficient cleavage of gem-diacetates to aldehydes by CBr4 . Synth. Commun. 2001 , 31 , 1091 – 1095 .
   Web of Science ®Google Scholar
• Zhang , Z. H. ; Yin , L. ; Wang , Y. M. ; Liu , J. Y. ; Li , Y. Indium tribromide in poly(ethylene glycol)(PEG): A novel and efficient recycle system for chemoselective deprotection of 1,1-diacetates . Green Chem. 2004 , 6 , 563 – 565 .
   Web of Science ®Google Scholar