BF₃·OEt₂: An Efficient Catalyst for Transesterification of β-Ketoesters

REFERENCES

• (a) Benetti , S. ; Romagnoli , R. ; De Risi , C. ; Spalluto , G. ; Zanirato , V. Mastering β-keto esters . Chem. Rev. 1995 , 95 , 1065 – 1114 ; (b) Fujita , T. ; Tanaka , M. ; Norimine , Y. ; Sakai , H. S. Enantioselective synthesis of (−)-curcumanolide a using enzymatic transesterification of meso-spirodiol . J. Org. Chem. 1997 , 62 , 3824 – 3830 ; (c) Shapiro , G. ; Marzi , M. Facile and selective O-alkyl transesterification of primary carbamates with titanium(IV) alkoxides . J. Org. Chem. 1997 , 62 , 7096 – 7097 .
   Web of Science ®Google Scholar
• Mandai , T. ; Kuroda , A. ; Okumoto , H. ; Nakanishi , K. ; Mikuni , K. ; Hara , K. ; Hara , K. Synthesis of new baccatin III derivatives through transesterification of β-keto esters with a protected 10-deacetylbaccatin III . Tetrahedron Lett. 2000 , 41 , 239 – 242 .
   Web of Science ®Google Scholar
• Ward , R. S. Synthesis of podophyllotoxin and related compounds . Synthesis 1992 , 719 – 730 .
   Google Scholar
• Hoffmann , R. W. ; Helbig , W. ; Ladner , W. Synthesis of 6S,7S-anhydro-serricornine . Tetrahedron Lett. 1982 , 23 , 3479 – 3482 .
   Google Scholar
• Gilbert , J. C. ; Kelly , T. A. A diastereoselective synthesis of (±) trichodiene. Tetrahedron Lett. 1989, 30, 4193–4196.
   Google Scholar
• Otera , J. Transesterification . Chem. Rev. 1993 , 93 , 1449 – 1470 .
   Web of Science ®Google Scholar
• Chavan , S. P. ; Zubaidha , P. K. ; Dantale , S. W. ; Keshavaraja , A. ; Ramaswamy , A. V. ; Ravindranathan , T. Use of solid superacid (sulphated SnO2) as efficient catalyst in tacile transesterification of ketoesters . Tetrahedron Lett. 1996 , 37 , 233 – 236 .
   Web of Science ®Google Scholar
• Bandgar , B. P. ; Uppalla , L. S. ; Sadavarte , V. S. Envirocat EPZG and natural clay as efficient catalysts for transesterification of β-keto esters . Green Chem. 2001 , 3 , 39 – 41 .
   Web of Science ®Google Scholar
• Jin , T. ; Zhang , S. ; Li , T. Transesterification of β-ketoesters with alcohols catalyzed by montmorillonite K-10 . Green Chem. 2002 , 4 , 32 – 34 .
   Web of Science ®Google Scholar
• Madje , B. R. ; Patil , P. T. ; Shindalkar , S. S. ; Benjamin , S. B. ; Shingare , M. S. ; Dongare , M. K. Facile transesterification of β-ketoesters under solvent-free condition using borate zirconia solid acid catalyst . Catal. Commun. 2004 , 5 , 353 – 357 .
   Web of Science ®Google Scholar
• Sairre , M. I. D. ; Bronze-Uhle , E. S. ; Donate , P. M. Niobium(V) oxide: A new and efficient catalyst for the transesterification of β-keto esters . Tetrahedron Lett. 2005 , 46 , 2705 – 2708 .
   Web of Science ®Google Scholar
• (a) Pandey , R. K. ; Kumar , P. A facile procedure for transesterification of β-keto esters promoted by ceria-yttria based Lewis acid catalyst . Catal. Commun. 2007 , 8 , 1122 – 1125 ; (b) Kumar , P. ; Pendey , R. K. A facile and selective procedure for transesterification of β-keto esters promoted by yttria-zirconia based Lewis acid catalyst . Synlett 2000 , 2 , 251 – 253 .
   Google Scholar
• (a) Balaji , B. S. ; Sasidharan , M. ; Kumar , R. ; Chanda , M. A facile and selective synthesis of β-keto esters via zeolite catalysed transesterification . Chem. Commun. 1996 , 707 – 708 ; (b) Balaji , B. S. ; Chanda , B. M. Simple and high-yielding syntheses of β-keto esters catalysed by zeolites . Tetrahedron 1998 , 54 , 13237 – 13252 ; (c) Sasidharan , M. ; Kumar , R. Transesterification over various zeolites under liquid-phase conditions . J. Mol. Catal. A: Chem. 2004 , 210 , 93 – 98 ; (d) Chavan , S. P. ; Pasupathy , K. ; Shengule , S. ; Shinde , V. ; Anand , R. Catalytic transesterification of β-ketoesters with H-FER under solvent-free conditions . Arkivoc 2005 , 162 – 168 .
   Google Scholar
• Chavan , S. P. ; Kale , R. R. ; Shivasankar , K. ; Chandake , S. I. ; Benjamin , S. B. A simple and efficient method for transesterification of β-ketoesters catalysed by iodine . Synthesis 2003 , 2695 – 2698 ; (b) Chavan , S. P. ; Shivasankar , K. ; Sivappa , R. ; Kale , R. Zinc-mediated transesterification of β-ketoesters and coumarin synthesis . Tetrahedron Lett. 2002 , 43 , 8583 – 8586 .
   Google Scholar
• Chavan , S. P. ; Subbarao , Y. T. ; Dantale , S. W. ; Sivappa , R. Transterification of ketoesters using Amberlyst-15 . Synth. Commun. 2001 , 31 , 289 – 294 .
   Web of Science ®Google Scholar
• Wang , B. ; Yang , L.-M. ; Suo , J.-S. Ionic liquid-regulated sulfamic acid: Chemoselective catalyst for the transesterification of β-ketoesters . Tetrahedron Lett. 2003 , 44 , 5037 – 5039 .
   Web of Science ®Google Scholar
• Kimel , W. ; Cope , A. C. The rearrangement of allyl-type esters of β-keto acids . J. Am. Chem. Soc. 1943 , 65 , 1992 – 1998 ; (b) Kimel , W. ; Sax , N. W. ; Kaiser , S. ; Eichmann , G. G. ; Chase , G. O. ; Ofner , A. Total synthesis of pseudoionone and an isomeric ketone . J. Org. Chem. 1958 , 23 , 153 – 157 .
   Google Scholar
• Kondaiah , G. C. M. ; Reddy , L. A. ; Babu , K. S. ; Gurav , V. M. ; Huge , K. G. ; Bandichhor , R. ; Reddy , P. P. ; Bhattacharyaa , A. ; Ananda , R. V. Boric acid: An efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate . Tetrahedron Lett. 2008 , 49 , 106 – 109 .
   Web of Science ®Google Scholar