FeCl₃‐Catalyzed Nucleophilic Substitution of Baylis–Hillman Adducts with Alcohols

References

• Ciganek , E. 1997 . Org. React. , 51 : 201
   Web of Science ®Google Scholar
• Basavaiah , D. , Rao , P. D. and Hyma , R. S. 1996 . The Baylis‐Hillman reaction: A novel carbon‐carbon bond forming reaction . Tetrahedron , 52 : 8001
   Web of Science ®Google Scholar
• Basavaiah , D. , Rao , A. J. and Satyanarayana , T. 2003 . Recent advances in the Baylis‐Hillman reaction and applications . Chem. Rev. , 103 : 811
   PubMed Web of Science ®Google Scholar
• Ramachandran , P. V. , Madhi , S. , Bland‐Berry , L. , Reddy , M. V. R. M. and O'Donnel , J. 2005 . Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition‐elimination of activated allylic acetates under chiral PTC conditions . J. Am. Chem. Soc. , 127 : 13450
   Google Scholar
• Kabalka , G. , Venkataiah , W. B. and Dong , G. 2005 . Palladium‐catalyzed regio‐ and stereoselective cross‐coupling of Baylis‐Hillman adducts and bimetals: a novel method for the synthesis of substituted allylsilanes and allylgermanes . Organometallics , 24 : 762 – 764 .
   Google Scholar
• Chung , Y. M. , Gong , J. H. , Kim , T. H. and Kim , J. N. 2001 . Synthesis of ethyl 3‐cyano‐2‐methylcinnamates and 3‐cyano‐2‐methylcinnamonitriles from the Baylis–Hillman acetates . Tetrahedron Lett. , 42 : 9023
   Web of Science ®Google Scholar
• Singh , V. , Saxena , R. and Batra , S. 2005 . Simple and efficient synthesis of substituted 2‐pyrrolidinones, 2‐pyrrolones, and pyrrolidines from enaminones of Baylis‐Hillman derivatives of 3‐isoxazolecarbaldehydes . J. Org. Chem. , 70 : 353
   PubMed Web of Science ®Google Scholar
• Patra , A. , Roy , A. K. , Batra , S. and Bhaduri , A. P. 2003 . NaBH4‐mediated facile reduction of esters of Baylis‐Hillman adducts: An efficient approach to substituted propane‐1,3‐Diols . Synlett , : 1819
   Google Scholar
• Radha Krishna , P. , Nasingam , M. and Kannan , V. 2004 . Use of a Baylis–Hillman adduct in the stereoselective synthesis of syributins via a RCM protocol . Tetrahedron Lett. , 45 : 4773
   Google Scholar
• Rodgen , S. A. and Schaus , S. E. 2006 . Efficient construction of the Clerodane Decalin Core by an asymmetric Morita‐Baylis‐Hillman reaction/Lewis acid promoted annulation strategy . Angew. Chem., Int. Ed. , 45 : 4929
   Google Scholar
• Drewes , S. E. and Roos , G. H. P. 1988 . Synthetic potential of the tertiary‐amine‐catalysed reaction of activated vinyl carbanions with aldehydes . Tetrahedron , 44 : 4653
   Web of Science ®Google Scholar
• Brzezinski , L. J. , Rafel , S. and Leahy , J. M. 1997 . The asymmetric Baylis‐Hillman reaction . J. Am. Chem. Soc. , 119 : 4317
   Web of Science ®Google Scholar
• Wori , W. , Kuroda , S. and Dekura , F. 1999 . Formation of silazirconacyclopentene via Zirconium‐Silene complex and alkyne . J. Am. Chem. Soc. , 121 : 5591
   Google Scholar
• Trost , B. M. , Thiel , O. R. and Tsui , H. C. 2003 . Total syntheses of furaquinocin A, B, and E . J. Am. Chem. Soc. , 125 : 13155
   Google Scholar
• Basavaiah , D. and Kumaragurubaran , N. 2001 . The Baylis–Hillman chemistry in aqueous media: a convenient synthesis of 2‐methylenealkanoates and alkanenitriles . Tetrahedron Lett. , 42 : 477
   Web of Science ®Google Scholar
• Kim , J. N. , Lee , H. J. , Lee , K. Y. and Gong , J. H. 2002 . Regioselective allylic amination of the Baylis‐Hillman adducts: An easy and practical access to the Baylis‐Hillman adducts of N ‐Tosylimines . Synlett , : 173
   Google Scholar
• Basavaiah , D. , Reddy , R. J. and Rao , J. S. 2006 . Applications of Baylis–Hillman adducts: a simple, convenient, and one‐pot synthesis of 3‐benzoylquinolines . Tetrahedron Lett. , 47 : 73
   Google Scholar
• Basavaiah , D. , Suguna , H. R. , Muthukumaran , K. and Kumaragurubaran , N. 2000 . Synthetic applications of the Baylis–Hillman Adducts: A simple stereoselective synthesis of (E)‐3‐(Nitroxymethyl)alk‐3‐en‐2‐ones . Tetrahedron , 56 : 5905
   Google Scholar
• Basavaiah , D. , Suguna , H. R. , Padmaja , K. and Krishnamacharyulu , M. 1999 . The Baylis‐Hillman reaction: An expedient synthesis of (Z)‐keto allyl bromides and chlorides . Tetrahedron , 55 : 6971
   Web of Science ®Google Scholar
• Basavaiah , D. , Suguna , H. R. , Muthukumaran , K. and Kumaragurubaran , N. 2000 . Stereoselective transformation of Baylis‐Hillman adducts into (3E)‐3‐(Alkoxymethyl)alk‐3‐en‐2‐ones . Synthesis , : 217
   Google Scholar
• Cho , C. W. and Krische , M. J. 2004 . Regio‐ and stereoselective construction of γ‐butenolides through phosphine‐catalyzed substitution of Morita‐Baylis‐Hillman acetates: an organocatalytic allylic alkylation . Angew. Chem., Int. Ed. , 43 : 6689
   PubMed Web of Science ®Google Scholar
• Cho , C. W. , Kong , J. R. and Krische , M. J. 2004 . Phosphine‐catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita‐Baylis‐Hillman acetates . Org. Lett. , 6 : 1337
   PubMed Web of Science ®Google Scholar
• Park , H. , Cho , C. W. and Krische , M. J. 2006 . Phosphine‐catalyzed allylic substitution of Morita‐Baylis‐Hillman acetates: synthesis of N‐protected β‐Aminophos‐ phonic Acid esters . J. Org. Chem. , 71 : 7892
   Google Scholar
• Wang , L. C. , Luiz , A. L. , Agapiou , K. , Jang , H. Y. and Krischer , M. J. 2002 . Organocatalytic Michael Cycloisomerization of Bis(enones): The Intramolecular Rauhut‐Currier Reaction . J. Am. Chem. Soc. , 124 : 2402
   Google Scholar
• Jellerichs , B. G. , Kong , J. R. and Krischer , M. J. 2003 . Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis . J. Am. Chem. Soc. , 125 : 7758
   Google Scholar
• Roy , O. , Riahi , A. , Henin , F. and Muzart , T. 2000 . Synergy or competition between palladium‐catalysis and KF/Alumina‐mediation for the allylic substitution of the acetates of Baylis–Hillman adducts by phenols . Tetrahedron , 56 : 8133
   Google Scholar
• Trost , B. M. and Toste , D. F. 2000 . Deracemization of Baylis‐Hillman adducts . J. Am. Chem. Soc. , 122 : 3534 – 3535 .
   Google Scholar
• Kim , J. N. , Lee , H. J. and Gong , J. H. 2002 . Synthesis of enantiomerically enriched Baylis–Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate . Tetrahedron Lett. , 43 : 9141
   Google Scholar
• Trost , B. M. , Thiel , O. R. and Tsui , H. C. 2002 . DYKAT of Baylis‐Hillman Adducts: Concise total synthesis of furaquinocin E . J. Am. Chem. Soc. , 124 : 11616
   Google Scholar
• Trost , B. M. , Calkins , T. L. , Oertelt , C. and Zambrano , J. 1998 . Catalyst controlled diastereoselective N‐alkylations of α‐amino esters . Tetrahedron Lett. , 39 : 1713
   Google Scholar
• Rajesh , S. , Banerji , B. and Iqbal , J. 2002 . Palladium(0)‐catalyzed regioselective synthesis of α‐dehydro‐β‐amino esters from amines and allyl acetates: synthesis of a α‐dehydro‐β‐amino acid derived cyclic peptide as a constrained‐β‐Turn mimic . J. Org. Chem. , 67 : 7852
   PubMed Web of Science ®Google Scholar
• Trost , B. M. , Machacek , M. R. and Tsui , H. C. 2005 . Development of aliphatic alcohols as nucleophiles for palladium‐catalyzed DYKAT reactions: Total synthesis of (+)‐hippospongic acid A . J. Am. Chem. Soc. , 127 : 7014
   PubMed Web of Science ®Google Scholar
• Li , J. , Wang , X. X. and Zhang , Y. M. 2005 . Remarkable rate acceleration of water‐promoted nucleophilic substitution of Baylis–Hillman acetate: a facile and highly efficient synthesis of N‐substituted imidazole . Tetrahedron Lett. , 46 : 5233
   Web of Science ®Google Scholar
• Li , J. , Wang , X. X. and Zhang , Y. M. 2005 . Direct and highly efficient synthesis of (Z)‐allyl iodides from Baylis‐Hillman adducts promoted by TMSCl/NaI system . Synlett , : 1039
   Google Scholar
• Li , J. , Qian , W. X. and Zhang , Y. M. 2004 . SmI2‐mediated elimination reaction of Baylis–Hillman adducts controlled by temperature: a facile synthesis of trisubstituted alkenes and 1,5‐hexadiene derivatives with E‐stereoselectivity . Tetrahedron , 60 : 5793
   Google Scholar
• Li , S. Y. , Li , J. and Jia , X. S. 2007 . Samarium metal promoted facile C‐Acetylation of Baylis‐Hillman adducts in the presence of iron(III) chloride and iodine . Synlett , 7 : 1115
   Google Scholar
• Bolm , C. , Legros , J. , Le Paih , J. and Zani , L. 2004 . Iron‐Catalyzed Reactions in Organic Synthesis . Chem. Rev. , 104 : 6217
   PubMed Web of Science ®Google Scholar
• Choudhary , V. R. , Jana , S. K. and Kiran , B. P. 1999 . Alkylation of benzene by benzyl chloride over H‐ZSM‐5 zeolite with its framework Al completely or partially substituted by Fe or Ga . Catal. Lett. , 59 : 217
   Google Scholar
• Choudhary , V. R. and Jana , S. K. 2002 . Benzylation of benzene by benzyl chloride over Fe‐, Zn‐, Ga‐ and In‐modified ZSM‐5 type zeolite catalyst . Appl. Catal. A , 224 : 51
   Web of Science ®Google Scholar
• Pai , S. G. , Bajpai , A. R. , Deshpande , A. B. and Samant , S. D. 1997 . Friedel‐Crafts Benzylation of Arenes Using FeCl3 Impregnated Montmorillonite K10 . Synth. Commun. , 27 : 2267
   Web of Science ®Google Scholar
• Pai , S. G. , Bajpai , A. R. , Deshpande , A. B. and Samant , S. D. 2000 . Benzylation of arenes in the presence of Montmorillonite K10 modified using aqueous and acetonitrile solutions of FeCl3 . J. Mol. Catal. A , 156 : 233
   Google Scholar