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cyclosiomerization of (Z)-enynols into furans: f) A. E. Díaz-Álvarez, P. Crochet, M. Zablocka, C. Duhayon, V. Cadierno, J. Gimeno, J. P. Majorai, Adv. Synth. Catal. 2006, 345, 1671-1679.
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cyclosiomerization of (Z)-enynols into furans: f) A. E. Díaz-Álvarez, P. Crochet, M. Zablocka, C. Duhayon, V. Cadierno, J. Gimeno, J. P. Majorai, Adv. Synth. Catal. 2006, 345, 1671-1679.
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For reviews and books covering the burgeoning role of ruthenium catalysts in organic synthesis see: a
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j) Ruthenium Catalyzed Processes, (Guest Ed.: J. Gimeno), in: Curr. Org. Chem. 2006, 10, 113-225 (a thematic issue devoted to this topic).
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28944434611
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We note that the dinuclear Ru(III) species [Cp*Ru(μ2- XMe)2RuCp*(OH2, OTf]2 (X, S, Se, Te) are also able to catalyze related C-C coupling reactions between propargylic alcohols and acetone: G. Onodera, H. Matsumoto, Y. Nishibayashi, S. Uemura, Organometallics 2005, 24, 5799-5801
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2 (X = S, Se, Te) are also able to catalyze related C-C coupling reactions between propargylic alcohols and acetone: G. Onodera, H. Matsumoto, Y. Nishibayashi, S. Uemura, Organometallics 2005, 24, 5799-5801.
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34547227895
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We note that, although monosubstituted alkynols HC≡ CC(OH)HR (R, aryl group) also undergo the Meyer-Schuster isomerization into enals in the presence of complex 1 (see ref.[4, attempts to promote its one-pot coupling with acetone resulted in the formation of the corresponding (EE)-dienones · RCH=CHCH=C(H)C(= O)Me (C) in remarkably low yieldssee ref.[3, The monitoring of these reactions by GC showed, in addition to the complete consumption of the starting propargylic alcohol, that some uncharacterized by-products are also formed pointing out the existence of competitive processes in solution involving probably furan ring formation
-
[3]). The monitoring of these reactions by GC showed, in addition to the complete consumption of the starting propargylic alcohol, that some uncharacterized by-products are also formed pointing out the existence of competitive processes in solution involving probably furan ring formation.
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22
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33845374099
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For general reviews on its occurrence and applications see: a
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For general reviews on its occurrence and applications see: a) B. H. Lipshutz, Chem. Rev. 1986, 86, 795-820;
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b) R. Benassi, in : Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, vol. 2, pp. 259-295;
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34547230366
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H. Heaney, J. S. Ahn, in: Comprehensive Heterocyclic Chemistry II, (Eds. : A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, 2, pp. 297-350;
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d)W. Friedrichsen, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, vol. 2, pp. 351-393;
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B.A. Keay, P. W. Dibble, in: Comprehensive Heterocyclic Chemistry II, (Eds. : A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, 2, pp. 395-436;
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f) X. L. Hou, Z. Yang, H. N. C. Wong, in: Progress in Heterocyclic Chemistry, (Eds.: C. W Gribble, T. L. Gilchrist), Pergamon Press, Oxford, 2003, vol. 15, pp. 167-205.
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28
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0032485365
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For recent reviews on the synthesis of furans see: a
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For recent reviews on the synthesis of furans see: a) X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong, H. N. C. Wong, Tetrahedron 1998, 54, 1955-2020;
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34547145943
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2].
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2].
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34
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2442701969
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4 (10 mol%), has been recently reported: Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura, J. Org. Chem. 2004, 69, 3408-3412.
-
4 (10 mol%), has been recently reported: Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura, J. Org. Chem. 2004, 69, 3408-3412.
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35
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0038112039
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Formation of tri- and tetrasubstituted furans from secondary propargylic alcohols and enolizable ketones, in the presence of catalytic amounts of [Cp*RuCl(μ2-SMe)2RuCp*Cl, 10 mol, NH4BF4 (20 mol, and PtCl2 (20 mol, has been reported. This process involves also the initial formation of a γ-ketoalkyne, via Ru-catalyzed propargylic substitution of the alkynol with the ketone, which undergoes a Pt-catalyzed Markovnikov hydration of the alkyne moiety to give a 1,4-diketone. Subsequent cyclization of this diketone, also catalyzed by Pt, generates the final furans. We note that (i) no 1,3-dicarbonyl compounds were used as substrates in this catalytic reaction, and (ii) the process is only operative with terminal alkynols HC≡CC(OH)-HAr Ar, aryl group, Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S. Uemura, Angew. Chem. Int. Ed. 2003, 42, 2681-2684
-
2 (20 mol%), has been reported. This process involves also the initial formation of a γ-ketoalkyne, via Ru-catalyzed propargylic substitution of the alkynol with the ketone, which undergoes a Pt-catalyzed Markovnikov hydration of the alkyne moiety to give a 1,4-diketone. Subsequent cyclization of this diketone, also catalyzed by Pt, generates the final furans. We note that (i) no 1,3-dicarbonyl compounds were used as substrates in this catalytic reaction, and (ii) the process is only operative with terminal alkynols HC≡CC(OH)-HAr (Ar = aryl group): Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S. Uemura, Angew. Chem. Int. Ed. 2003, 42, 2681-2684.
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36
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34547156780
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7CCCO)].
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7CCCO)].
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37
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33744818185
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The Boc group is known to be a versatile and widely used protecting group for carboxylic acids. Several methods have been reported for its removal, most of them involving the use of Brønsted (HCl, H2SO4, HNO3 or CF3CO2H) or Lewis (I2, TiCl4, ZnBr2, CeCl3, SiO2 or silyl triflates) acids. Representative references are the following: a) J. S. Yadav, E. Balanarsaiah, S. Raghavendra, M. Satyanarayana, Tetrahedron Lett. 2006, 47, 4921-4924;
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2 or silyl triflates) acids. Representative references are the following: a) J. S. Yadav, E. Balanarsaiah, S. Raghavendra, M. Satyanarayana, Tetrahedron Lett. 2006, 47, 4921-4924;
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34547234266
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The carboxylic acid 12a could not be detected by GC/ MS pointing out that its decarboxylation is a highly favoured process.
-
The carboxylic acid 12a could not be detected by GC/ MS pointing out that its decarboxylation is a highly favoured process.
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3 which undergoes the addition of the nucleophile (in our case the enolic form of the 1,3-dicarbonyl compound acts as a carbon-centered nucleophile): R. Sanz, A. Martínez, J. M. Álvarez-Gutiérrez, F. Rodriguez, Eur. J. Org. Chem. 2006, 1383-1386;
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3 which undergoes the addition of the nucleophile (in our case the enolic form of the 1,3-dicarbonyl compound acts as a carbon-centered nucleophile): R. Sanz, A. Martínez, J. M. Álvarez-Gutiérrez, F. Rodriguez, Eur. J. Org. Chem. 2006, 1383-1386;
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it should be also noted that very recently two general and highly efficient procedures for the propargylic substitution of alkynols catalyzed by the Lewis acids BiCl3 and FeCl3 have been reported: Z.-P. Zhan, W.-Z. Yang, R.-F. Yang, X-L. Yu, J.-P. Li, H.-J. Liu, Chem. Commun. 2006, 3352-3354;
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3 have been reported: Z.-P. Zhan, W.-Z. Yang, R.-F. Yang, X-L. Yu, J.-P. Li, H.-J. Liu, Chem. Commun. 2006, 3352-3354;
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Although complex 1 is known to be an active catalyst in propargylic substitution processes of alkynols with alcohols (see ref.[4a, it is not active at all when carboncentered nucleophiles, such as enolizable ketones, are used as substrates see ref.[3
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[3]).
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67
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In accord with previous results, the treatment of 2a with methyl acetoacetate and complex 1 (5 mol, at 75°C and in the absence of CF 3CO2H, results in the exclusive formation of enal (E)-RHC=CHCHO (R, 1-naphthyl) as the result of the Meyer-Schuster isomerization of the alkynol see ref.[4b
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[4b]).
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68
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It should be noted that other ruthenium(II) sources, such as [RuCl 2(PPh3)3, RuCl2(DMSO) 4, RuCl(μ-Cl)(η6-p-cymene)}2, RuCl(η5-C5H5)(PPh3) 2, RuCl(η5-C9H7)(PPh 3)2] and [Ru(η3-C3H 4Me)2(COD, were also found to be operative in this furan-ring formation reaction. Nevertheless, their efficiency is by far lower than that shown by complex 1. Thus, using the coupling of alkynol 2c with ethyl acetoacetate as a model reaction, 2c, ethyl acetoacetate, CF 3CO2H, Ru] ratio, 20:200:10:1, the best results were obtained using [RuCl2(DMSO)4] and [Ru(η3-2- C3H4Me)2(COD, which give furan 8c in 60, and 64, yield GC determined, respectively, after
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2(COD)] which give furan 8c in 60 % and 64 % yield (GC determined), respectively, after 8 h (to be compared with entry 4 in Table 2).
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