Copper Triflate–Catalyzed Cross‐Aldol Condensation: A Facile Synthesis of α,α′‐Bis(Substituted Benzylidene) Cycloalkanones

References

• Han , Z. , Vehora , S. , Shinokubo , H. and Oshima , K. 2001 . TiCl4‐n‐Bu4NX (X=I, Br, and Cl) combination‐induced coupling of α,β‐unsaturated ketones with aldehydes . J. Org. Chem. , 66 : 7854 – 7857 .
   PubMed Web of Science ®Google Scholar
• Kakumoto , K. , Kobayashi , S. and Sugiura , M. 2002 . Transition metal salts–catalyzed Aza–Michael reactions of enones with carbamates . Org. Lett. , 4 : 1319 – 1322 .
   PubMed Web of Science ®Google Scholar
• Murray , R. J. and Cromwell , N. H. 1976 . Mobile keto allyl systems 18. Synthesis and charge‐transfer interactions of 2‐(alpha‐aminobenzyl)‐1‐indenones . J. Org. Chem. , 41 : 3540 – 3545 .
   Web of Science ®Google Scholar
• Sinisterra , J. V. and Garcia‐Raso , A. 1984 . An improved procedure for the Claisen–Schmidt reaction . Synthesis , : 502 – 503 .
   Web of Science ®Google Scholar
• Irie , K. and Watanabe , K. 1980 . Aldol condensation with metal(II) complex catalysts . Bull. Chem. Soc. Jpn. , 53 : 1366 – 1371 .
   Web of Science ®Google Scholar
• Iranpoor , N. and Kazemi , F. 1998 . RuCl3 catalyses aldol condensations of aldehydes and ketones . Tetrahedron , 54 : 9475 – 9480 .
   Web of Science ®Google Scholar
• Deng , G. and Ren , T. 2003 . Indium trichloride catalyzes aldol condensations of aldehydes and ketones . Synth. Commun. , 33 : 2995 – 3001 .
   Web of Science ®Google Scholar
• Nakano , T. and Migita , T. 1993 . A convenient synthesis of α,α′‐bis(substituted benzylidene) cycloalkanones . Chem. Lett. , 12 : 2157 – 2158 .
   Web of Science ®Google Scholar
• Nakano , T. , Irifune , S. , Umano , S. , Inada , A. , Ishii , Y. and Ogawa , M. 1987 . Cross‐condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes . J. Org. Chem. , 52 : 2239 – 2244 .
   Web of Science ®Google Scholar
• Mahrwald , R. and Schick , H. 1990 . Synthesis of α,ß‐unsaturated carbonyl compounds by titanium tetraalkoxide–induced aldol condensation under neutral conditions . Synthesis , : 592 – 595 .
   Web of Science ®Google Scholar
• Iranpoor , N. , Zeynizadeh , B. and Aghapour , A. 1999 . Aldol condensation of cycloalkanones with aromatic aldehydes catalysed with TiCl3(SO3CF3) . J. Chem. Res., Synop. , : 554 – 555 .
   Web of Science ®Google Scholar
• Zheng , M. , Wang , L. , Shao , J. and Zhong , Q. 1997 . A facile synthesis of α,α′‐bis(substituted benzylidene) cycloalkanones catalyzed by bis(p‐ethoxyphenyl) telluroxide (BMPTO) under microwave irradiation . Synth. Commun. , 27 : 351 – 354 .
   Web of Science ®Google Scholar
• Li , J. , Yang , W. , Chen , G. and Li , T. 2003 . A facile synthesis of α,α′‐bis(substituted benzylidene) cycloalkanones catalyzed by KF/Al2O3 under ultrasound irradiation . Synth. Commun. , 33 : 2619 – 2625 .
   Web of Science ®Google Scholar
• Sabitha , G. , Reddy , G. S. K. K. , Reddy , B. and Yadav , J. S. 2004 . Iodotrimethylsiane‐mediated cross‐aldol condensation: A facile synthesis of α,α′‐bis(substituted benzylidene) cycloalkanones . Synthesis , : 263 – 266 .
   Web of Science ®Google Scholar
• Li , Z. , Zhang , Y. and Li , Q. 2000 . Samarium(III) iodide promoted preparation of α,α′‐bis (substituted benzylidene) cyclohexanones from benzaldehydes and cyclohexanone . J. Chem. Res., Synop. , : 580 – 581 .
   Web of Science ®Google Scholar
• Kobayashi , S. , Sugiura , M. , Kitagawa , H. and Lam , W.‐L. 2002 . Rare‐earth metal triflates in organic synthesis . Chem. Rev. , 102 : 2227 – 2302 .
   PubMed Web of Science ®Google Scholar
• Hachiya , I. and Kobayshi , S. 1993 . Aqueous reactions with a Lewis acid and an organometallic reagent. The scandium trifluoromethanesulfonate‐catalyzed allylation reaction of carbonyl compounds with tetraallyltin . J. Org. Chem. , 58 : 6958 – 6960 .
   Web of Science ®Google Scholar
• Wang , L. , Sheng , J. , Tian , H. , Han , J. , Fan , Z. and Qian , C. 2004 . A convenient synthesis of α,α′‐bis(substituted benzylidene) cycloalkanones catalyzed by Yb(OTf)3 under solvent‐free conditions . Synthesis , : 3060 – 3064 .
   Web of Science ®Google Scholar
• Su , W. and Jin , C. 2004 . Ytterbium triflate–catalyzed Friedel–Crafts reaction: Facile synthesis of diaryl ketones . Synth. Commun. , 34 : 4249 – 4256 .
   Web of Science ®Google Scholar
• Su , W. and Li , J. 2004 . Highly selective Friedel–Crafts monoacylation of ferrocene catalyzed by ytterbium(III) triflate . J. Chem. Res., Synop. , : 552 – 553 .
   Web of Science ®Google Scholar