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Synthesis 2006(7): 1099-1102
DOI: 10.1055/s-2006-926346
DOI: 10.1055/s-2006-926346
PAPER
© Georg Thieme Verlag Stuttgart · New York
Amine-Catalyzed Aldol Condensation in the Presence of Lithium Perchlorate
Weitere Informationen
Received
27 July 2005
Publikationsdatum:
27. Februar 2006 (online)
Publikationsverlauf
Publikationsdatum:
27. Februar 2006 (online)
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Abstract
A catalytic aldol condensation in the presence of lithium perchlorate and tertiary amines is described giving pure products in high yields. The aldol condensation can be performed even in the presence of hydrated lithium perchlorate.
Key words
aldol reactions - aldehydes - ketones - catalysis - amines
-
1a
Nakano T.Irifune S.Inada A. J. Org. Chem. 1987, 52: 2239 -
1b
Ogawa M,Ishii Y,Nakano T, andIrifune S. inventors; Jpn. Kohai Tokkyo JP 63192446 A2. ; Chem. Abstr. 1988, 63, 238034 - 2
Deli J.Lorand T.Szabo D.Foldesi A. Pharmazie 1984, 39: 539 - 3
Kishore G.Kishore K. Polymer 1995, 36: 1903 -
4a
Adams KB.Ferstl EM.Davis MC.Herold M.Kurtkaya S.Camalier RF.Hollingshead MG.Kaur G.Sausville EA.Rickles FR.Snyder JP.Liotta DC.Shoji M. Bioorg. Med. Chem. 2004, 12: 3871 -
4b
Robinson TP.Hubbard RB.Ehlers TJ.Arbiser JL.Goldsmith DJ.Bown JP. Bioorg. Med. Chem. 2005, 13: 4007 - 5
Clarke TP.Höppe HAF.Lloyd-Jones GC.Murray M.Peakman TM.Stentiford RA.Walsh KE.Worthington PA. Eur. J. Org. Chem. 2000, 963 - 6
Arcadi A.Bianchi G.Chiarini M.Dànniballe G.Marinelli F. Synlett 2004, 944 - 7
Fairlamb IJS.Kapdi AR.Lee AF. Org. Lett. 2004, 6: 4435 -
9a Ti(OR)4:
Mahrwald R.Schick H. Synthesis 1990, 592 -
9b RuCl3:
Iranpoor N.Kazemi F. Tetrahedron 1998, 54: 9475 -
9c SmI3:
Bao WL.Zhang YM. Youji Huaxue 1998, 18: 272 -
9d FeCl3:
Zhang Fan XS.Niu HY.Wang JJ. Green Chem. 2003, 5: 267 -
9e BF3·Et2O:
Huang DF.Wang JX.Hu YL. Chem. Lett. 2003, 14: 333 -
9f InCl3:
Deng G.Ren T. Synth. Commun. 2003, 33: 2995 -
9g Yb(OTf)3:
Wang L.Scheng J.Han HT.Fan Z.Qian C. Synthesis 2004, 3060 -
9h For NaOH/H2O-system, see:
Fairlamb IJS. SyntheticPages 2004, 221 - 10
Markert M.Mahrwald R. Synthesis 2004, 1429 - 11 For safety information, see:
Armarego WLF.Perrin DD. Purification of Laboratory Chemicals Butterworth-Heinemann; Oxford: 1997. - 12
Ramalingam K.Berlin KD.Satyamurthy N.Sivakumar R. J. Org. Chem. 1979, 44: 471 - 13
Shoppee CW.Cooke BJA. J. Chem. Soc., Perkin Trans. 1 1973, 1026 -
14a
Wattanasin S.Murphy WS. Synthesis 1980, 647 -
14b
Suarez JAQ,Peseke K,Kordian M,Carvalho JE,Kohn LK,Antonio MA, andBrunhari H. inventors; PCT Int. Appl. 2004047716. (4d, 87% yield) - 15
Thiele G.Streitwieser A. J. Am. Chem. Soc. 1994, 116: 446 -
16a
Ocafrain M.Devaud M.Troupel M.Perichon J. J. Chem. Soc., Chem. Commun. 1995, 2331 -
16b
Binder J.Zbiral E. Tetrahedron Lett. 1984, 25: 4213 - 17
Frey H.Behmann G.Kaupp G. Chem. Ber. 1987, 120: 387 - 18
Kaupp G.Frey H.Behmann G. Chem. Ber. 1988, 121: 2127 - 19
Eldin S.Whalen DL.Pollack RM. J. Org. Chem. 1993, 58: 7100
References
Compound 4d: 1 g costs 600 $ (TRC Biomedical Research Chemicals).