Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2007 - Issue 1
108
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Cerium(IV) Triflate‐Catalyzed Selective Gem‐diacetylation of Aldehydes with Acetic Anhydride

&
Pages 77-84 | Received 15 May 2007, Published online: 25 Jan 2008

References

  • Kochhar , K. S. , Bal , B. S. , Deshpande , R. P. , Rajadhyaksha , S. N. and Pinnick , H. W. 1983 . Conversion of aldehydes into geminal diacetate . J. Org. Chem. , 48 : 1765
  • Held , H. , Rengstl , A. and Mayer , D. 1985 . Ullman's Encyclopedia of Industrial Chemistry Edited by: Gerhartz , W. Vol. A1 , 68 New York : VCH .
  • Jameleddine , K. and Denis , G. 1999 . Bicycloannelation reaction of γ‐substituted cyclic β‐keto esters . Synth. Commun. , 29 : 1929
  • Lu , X. and Huang , Y. 1986 . Allylic geminal diacetates as a a1, a3 synthon. A convenient synthesis of bicyclo[3.3.1]nonan‐9‐one derivatives . Tetrahedron Lett. , 27 : 1615
  • Holzapfel , C. W. , Marais , L. and Toerien , F. 1999 . Palladium‐catalyzed cyclization of chiral carbohydrate‐derived geminal diacetates . Tetrahedron , 55 : 3467
  • Frick , J. G. Jr. and Harper , R. J. Jr. 1984 . Acetals as crosslinking reagents for cotton . J. Appl. Polym. Sci. , 29 : 1433
  • Sanderson , W. R. Peroxygen compounds . Eur. Pat. Appl. EP125781 . 1985 . 57
  • Sandberg , M. and Sydnes , L. K. 1998 . The chemistry of acylals: Part II. Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of Lewis acid . Tetrahedron Lett. , 39 : 6361
  • Jadav , J. S. , Reddy , B. V. S. and Reddy , G. S. K. K. 2000 . Indium‐mediated allylation of gem‐diacetates to homoallylic acetates in aqueous media . Tetrahedron Lett. , 41 : 2695
  • Trost , B. M. and Lee , C. B. 2001 . Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part II. Scope and applications . J. Am. Chem. Soc. , 123 : 3687
  • Trost , B. M. and Lee , C. B. 2001 . gem‐Diacetates as carbonyl surrogates for asymmetric synthesis. Total synthesis of sphingofungins E and F . J. Am. Chem. Soc. , 123 : 12191
  • Gregory , M. J. 1970 . Evidence for a cyclic AA1 1 mechanism in the hydrolysis of benzylidene diacetates . J. Chem. Soc. B , : 1201
  • Olah , G. A. and Mehrotra , A. K. 1982 . Catalysis by solid superacids; 16. Improved nafion‐H catalysed preparation of 1,1‐diaceataes from aldehydes . Synthesis , : 962
  • Scriabine , I. 1961 . New method of preparation of dihydrocinnamic aldehydes . Bull. Soc. Chim. Fr. , : 1194
  • Michie , J. K. and Miller , J. A. 1981 . Phosphorus trichloride as a catalyst in the preparation of 1,1‐diacetates from aldehydes . Synthesis , : 824
  • Deka , N. , Kalita , D. J. , Borah , R. and Sarma , J. C. 1997 . Iodine as acetylation catalyst in the preparation of 1,1‐diacetates from aldehydes . J. Org. Chem. , 62 : 1563
  • Pereira , C. , Gigante , B. , Marcelo‐Curto , M. J. , Carreyre , H. , Perot , G. and Guisnet , M. 1995 . Diacetates from aldehydes in the presence of zeolites . Synthesis , : 1077
  • Aggarwal , V. K. , Fonquerna , S. and Vennall , G. P. 1998 . Sc(OTf)3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals); chemoselective protection of aldehydes in presence of ketones . Synlett , : 849
  • Chandra , K. L. , Saravanan , P. and Singh , V. K. 2000 . An efficient method for diacetylation of aldehydes . Synlett , : 359
  • Karimi , B. , Seradj , H. and Ebrahimian , G. R. 2000 . Mild and efficient conversion of aldehydes to 1,1‐diacetates catalysed with N‐bromosuccinimide (NBS) . Synlett , : 623
  • Carrigan , M. D. , Eash , K. J. , Oswald , M. C. and Mohan , R. S. 2001 . An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate . Tetrahedron Lett. , 42 : 8133
  • Karimi , B. , Ebrahimian , G. R. and Seradj , H. 2002 . Highly efficient and chemoselective conversion of aldehydes to acylals catalysed with tungsten hexachloride (WCl6) . Synth. Commun. , 32 : 669
  • Curini , M. , Epifano , F. , Marcotullio , M. C. , Rosati , O. and Nocchetti , M. 2002 . Preparation and deprotection of 1,1‐diacetates (acylals) using zirconium sulfophenyl phosphonate as catalyst . Tetrahedron Lett. , 43 : 2709
  • Yadav , J. S. , Reddy , B. V. S. , Venugopal , C. and Ramalingam , T. 2002 . LiBF4‐mediated conversion of aldehydes to gem‐diacetates . Synlett , : 604
  • Roy , S. C. and Banerjee , B. 2002 . A mild and efficient method for the chemoselective synthesis of acylals from aldehydes and their deprotection catalysed by ceric ammonium nitrate . Synlett , : 1677
  • Jin , T. S. , Sun , G. , Li , Y. W. and Li , T. S. 2002 . An efficient and convenient procedure for the preparation of 1,1‐diacetates from aldehydes catalysed by H2NSO3H . Green Chem. , 4 : 255
  • Reddy , A. V. , Ravinder , K. , Reddy , V. L. N. , Ravikanth , V. and Venkateswarlu , Y. 2003 . Amberlyst ‐15‐catalysed efficient synthesis of 1,1‐diacetates from aldehydes . Synth. Commun. , 33 : 1531
  • Firouzabadi , H. , Iranpoor , N. , Nowrouzi , F. and Amani , K. 2003 . Aluminium dodocatungstophosphate (AlPW12O40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diaceataes (acylals) under solvent‐free conditions . Tetrahedron Lett. , 44 : 3951
  • Ranu , B. C. , Dutta , J. and Das , A. 2003 . Zinc tetrafluoroborate‐catalysed efficient conversion of aldehydes to geminal diacetates and cyanoacetates . Chem. Lett. , 32 : 366
  • Karimi , B. and Maleki , J. 2003 . Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral conditions . J. Org. Chem. , 68 : 4951
  • Smitha , G. and Reddy , C. S. 2003 . A facile and efficient ZrCl4 catalyzed conversion of aldehydes to geminal‐diacetates and dipivalates and their cleavage . Tetrahedron , 59 : 9571
  • Aggen , D. H. , Arnold , J. N. , Hayes , P. D. , Smoter , N. J. and Mohan , R. S. 2004 . Bismuth compounds in organic synthesis. Bismuth nitrate catalysed chemoselective synthesis of acylals from aromatic aldehydes . Tetrahedron , 60 : 3675
  • Negron , G. E. , Palacios , L. N. , Angeles , D. , Lomas , L. and Gavino , R. 2005 . A mild and efficient method for the chemoselective synthesis of acylals from aromatic aldehydes and their deprotection catalyzed by sulfated zirconia . J. Braz. Chem. Soc. , 16 : 490
  • Bosco , J. W. J. , Purkayastha , N. , Raju , B. R. and Saikia , A. K. 2005 . Lithium chloride‐assisted chemoselective conversion of aldehydes into geminal diacetates under solvent‐free conditions . Synth. Commun. , 35 : 1301
  • Salavati‐Niasari , M. and Hydarzadeh , S. 2005 . An efficient method for the selective synthesis of geminal diacetates (acylals) from aromatic aldehydes using alumina‐supported InCl3 . J. Mol. Catal. A: Chem. , 237 : 254
  • Bartoli , G. , Cupone , G. , Dalpozzo , R. , Nino , A. D. , Maiuolo , L. , Procopio , A. , Sambri , L. and Tagarelli , A. 2002 . Deprotection of tert‐butyldimethylsilyl ethers promoted by cerium (IV) triflate . Tetrahedron Lett. , 43 : 5945
  • Khalafi‐Nezhad , A. and Fareghi Alamdari , R. 2001 . Efficient and catalytic deprotection of triphenylmethyl ethers with Ce(OTf)4 . Tetrahedron , 57 : 6805
  • Iranpur , N. , Firouzabadi , H. and Shekarize , M. 2003 . Micellar media for the efficient ring opening of epoxides with CN−, N3 −, NO3 −, NO2 −, SCN−, Cl− and Br− catalysed with Ce(OTf)4 . Org. Biomol. Chem. , 1 : 724
  • Iranpur , N. and Shekarriz , M. 1999 . Ring opening of epoxides with sodium cyanide catalysed with Ce(OTf)4 . Synth. Commun. , 29 : 2249
  • Iranpur , N. and Shekarriz , M. 1999 . Catalytic esterification of alcohols, carboxylic acids, and transesterification reactions with cerium(IV) triflate . Bull. Chem. Soc. Jpn. , 72 : 455

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.