One-step palladium-catalyzed synthesis of substituted dihydrofurans from the carbonate derivatives of γ-hydroxy-α,β-unsaturated sulfones

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9406-9413

  Garrido, José L ^a   Alonso, Inès ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; DIHYDROFURAN; FURAN DERIVATIVE; GAMMA HYDROXY ALPHA,BETA SULFONE; PALLADIUM; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032509260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981391r     Document Type: Article

References (60)

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2. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: New York, 1995; pp 290-422. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.; Semmelhack, M. F., Eds; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 3.3.
3. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: New York, 1995; pp 290-422. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.; Semmelhack, M. F., Eds; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 3.3.
4. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: New York, 1995; pp 290-422. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.; Semmelhack, M. F., Eds; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 3.3.
5. For palladium-catalyzed allylic substitutions in γ-oxygenated-α,β-unsaturated esters, see: (a) Suzuki, T.; Sato, T.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747. (b) Tanikaga, R.; Jun, T. X.; Kaji, A. J. Chem. Soc., Perkin Trans 1 1990, 1185. (c) Tsuda, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977. (d) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386. (e) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573. For substitutions on π-allylpalladium complexes substituted with carbonyl or cyano groups, see for instance: (f) Sugiura, M.; Yagi, Y.; Wei, S.-Y.; Nukai, T. Tetrahedron Lett. 1998, 39, 4351. (g) Hunt, D. A.; Quante, J. M.; Tyson, R. L.; Dasher, L. W. J. Org. Chem. 1984, 49, 5262. (h) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573. (i) Jackson, W. R.; Strauss, J. U. Aust. J. Chem. 1977, 30, 553.
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40. As it is shown below, the cyclization step is hardly regioselective from non symmetrically substituted 1,3-diketones (like benzoylacetone). (Equation Presented)
41. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103. (c) Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. (d) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. For a iodine-catalyzed cyclization of unsaturated 1,3-diketones, see: Antonioletti, R.; Cecchine, C.; Ciani, B; Magnanti, S. Tetrahedron Lett. 1995, 36, 9019.
42. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103. (c) Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. (d) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. For a iodine-catalyzed cyclization of unsaturated 1,3-diketones, see: Antonioletti, R.; Cecchine, C.; Ciani, B; Magnanti, S. Tetrahedron Lett. 1995, 36, 9019.
43. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103. (c) Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. (d) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. For a iodine-catalyzed cyclization of unsaturated 1,3-diketones, see: Antonioletti, R.; Cecchine, C.; Ciani, B; Magnanti, S. Tetrahedron Lett. 1995, 36, 9019.
44. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103. (c) Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. (d) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. For a iodine-catalyzed cyclization of unsaturated 1,3-diketones, see: Antonioletti, R.; Cecchine, C.; Ciani, B; Magnanti, S. Tetrahedron Lett. 1995, 36, 9019.
45. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1997, 38, 2103. (c) Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. (d) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. For a iodine-catalyzed cyclization of unsaturated 1,3-diketones, see: Antonioletti, R.; Cecchine, C.; Ciani, B; Magnanti, S. Tetrahedron Lett. 1995, 36, 9019.
46. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
47. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
48. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
49. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
50. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
51. 3 in THF at reflux, but not in the absence of either the phosphine or the palladium catalyst (no conversion was observed after 24 h in THF at 68°C). It seems plausible that in the presence of the palladium catalyst the phosphine might undergo the conjugate addition to the α,β-unsaturated sulfone to form a zwitterionic intermediate, which would act as a base converting 12a into its enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. For other phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett. 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. (c) Kim, B.; Kodomari, M.; Regen, S. L. J. Org. Chem. 1984, 49, 3233. (d) Baraldi, P. TG.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barcon, A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501. (e) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 3597.
52. 3 (5 mol %) and dppe as ligand (20 mol %), besides the dihydrofuran 17 (25% yield) significant amounts of disulfone 11 (40%) and 4-methyl-6-(phenylsulfonyl)hex-3,5-dien-2-one (12%) were detected. These side products would be likely the result of the competitive sulfonyl elimination on the π-allylpalladium intermediate.
53. Under the usual conditions (20 mol % of dppe) the yield in dihydrofurans 24 and 25 is lower due to the formation of an important amount of ethyl (E)-3-(p-tolylsulfonyl)-1-propen-1-yl carbonate.
54. Culvenor, C. C. J.; Davies, W.; Savige, W. E. J. Chem. Soc. 1949, 2198.
55. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
56. Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
57. For a review on the synthesis of substituted tetrahydrofurans, see: Bolvin, T. L. B. Tetrahedron 1987, 43, 3309.
58. Jandeleit, B. Ph.D. Dissertation, Aachen (Germany), 1995 (see also ref 5a).
59. Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Rudolph, M. P. W.; Wood, M. E. Tetrahedron 1997, 53, 5255.
60. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.