Synthesis of 3-substituted and 2,3-disubstituted 4-chlorofurans

Abstract

A simple method for the synthesis of 3-substituted and 2,3-disubstituted 4-chlorofurans is described which involves CuCl/bipy-catalysed regioselective cyclisation of 1-acetoxy-2,2,2-trichloroethyl allyl ethers followed successively by dechloroacetoxylation with Zn dust and tandem dehydrohalogenation–aromatisation with Bu^tOK/18-crown-6.

References

1. For a general review, see: X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong and H. N. C. Wong, Tetrahedron, 1998, 54, 1955 For some recent examples, see: J. W. Herndon and H. Wang, J. Org. Chem., 1998, 63, 4564; P. Wipf, L. T. Rahman and S. R. Rector, J. Org. Chem., 1998, 63, 7132; E. Bures, J. A. Nieman, S. Yu, P. G. Spinazzé, J.-L. J. Bontront, I. R. Hunt, A. Rauk and B. A. Keay, J. Org. Chem., 1997, 62, 8750; Y. R. Lee, N. S. Kim and B. S. Kim, Tetrahedron Lett., 1997, 38, 5671.
2. K. Nakanishi, Natural Products Chemistry, Kodansha, Tokyo, 1974.
3. The Chemistry of Heterocyclic Flavouring and Aroma Compounds, ed. G. Vernin, Ellis Horwood, Chichester, 1982.
4. For review, see: P. Bosshard and C. H. Eugster, Adv. Heterocycl. Chem., 1966, 7, 378; F. M. Dean, Adv. Heterocycl. Chem., 1982, 30, 167; D. M. X. Donnelly and M. J. Meegan, Comp. Heterocycl. Chem., 1984, 4, 657 For recent examples, see: K.-S. Chen and Y.-C. Wu, Tetrahedron, 1999, 55, 1353; A. Arnone, C. D. Gregorio, G. Nasini and O. V. De Pava, Tetrahedron, 1998, 54, 10199.
5. For review, see: (a) B. H. Lipshutz, Chem. Rev., 1986, 86, 795For some recent examples, see: (b) D. Meng and S. J. Danishefsky, Angew. Chem., Int. Ed., 1999, 38, 1485; (c) R. H. Mitchell, T. R. Ward, Y. Wang and P. W. Dibble, J. Am. Chem. Soc., 1999, 121, 2601; (d) W. E. Noland and B. L. Kedrowski, J. Org. Chem., 1999, 64, 596; (e) J. M. Harris, M. D. Keranen and G. A. O'Doherty, J. Org. Chem., 1999, 64, 2982; (f) A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem., 1999, 64, 3595; (g) A. Frustner and H. Weintritt, J. Am. Chem. Soc., 1998, 120, 2817; (h) M. Kurosu, L. R. Marcin, T. J. Grinsteiner and Y. Kishi, J. Am. Chem. Soc., 1998, 120, 6627.
6. T. Bach and L. Krüger, Tetrahedron Lett., 1998, 39, 1729; M. K. Wong, C. Y. Leung and H. N. C. Wong, Tetrahedron, 1997, 53, 3497; C. Alvarez-Ibarra, M. L. Quiroga and E. Toledano, Tetrahedron, 1996, 52, 4065; S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007; H. J. Reich and R. E. Olson, J. Org. Chem., 1987, 52, 2315; L. N. Pridgen and S. S. Jones, J. Org. Chem., 1982, 47, 1590.
7. C. Zhang, J. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; B. H. Lipshutz, P. A. Blomgren and S.-K. Kim, Tetrahedron Lett., 1999, 40, 197; X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno and W. H. Weinberg, Tetrahedron Lett., 1999, 40, 3855; B. H. Lipshutz and P. A. Blomgren, J. Am. Chem. Soc., 1999, 121, 5819; D. W. Old, J. P. Wolfe and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 9722; A. F. Littke and G. C. Fu, Angew. Chem., Int. Ed., 1998, 37, 3387; S. Saito, S. Oh-tani and N. Miyaura, J. Org. Chem., 1997, 62, 8024.
8. (a) R. C. Larock and C.-L. Liu, J. Org. Chem., 1983, 48, 2151 (poor yields); (b) Y. Tanabe, K.-i. Wakimura, Y. Nishii and Y. Muroya, Synthesis, 1996, 388 (2,5-diaryl-3-chlorofurans); (c) D. Obrecht, Helv. Chem. Acta., 1989, 72, 447 (2-substituted and 2,5-disubstituted 3-chlorofurans); (d) N. D. Ly and M. Schlosser, Helv. Chem. Acta., 1977, 60, 2085 (2-prenyl-3-chlorofuran); (e) R. E. Lutz and M. G. Reese, J. Am. Chem. Soc., 1959, 81, 127 (2,5-diaryl-3-chlorofurans).
9. In fact, we could find no report on 3-substituted 4-chlorofurans and only one report on 2,3-disubstituted 4-chlorofurans in which the formation of two 2,3-disubstituted 4-chlorofuran derivatives has been described. These chlorofurans were obtained as a mixture in poor yields, one of which was characterised only by GC-MS [ref. 8(a)].
10. L. Singh and R. N. Ram, J. Org. Chem., 1994, 59, 710; R. N. Ram and I. Charles, Tetrahedron, 1997, 53, 7335; R. N. Ram and L. Singh, Tetrahedron Lett., 1995, 36, 5401.
11. J. H. Udding, H. Hiemstra, M. N. A. Van Zanden and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 3123.
12. Although this scheme seems to be more attractive than Scheme 1, both in the number of steps and overall yields, we were not successful in preparing other trichloroethyl ethers by condensing trichloroethanol with secondary allylic halides.
13. P. F. Schuda, Top. Curr. Chem., 1980, 91, 75.
14. T. Saito, M. M. Suzuki, T. C. Akiyama, T. Takeuchi, T. Matsumoto and K. Suzuki, J. Am. Chem. Soc., 1998, 120, 11 633; S. Wadman, R. Whitby, C. Yeates, P. Kocienski and K. Cooper, J. Chem. Soc., Chem. Commun., 1987, 241; A. I. Meyers, C. J. Andres, J. E. Resek, Maureen A. Melaughlin, Charlotte C. Woodall and P. H. Lee, J. Org. Chem., 1996, 61, 2586; G. Vidari, G. Lanfranchi, P. Sartori and S. Serra, Tetrahedron: Asymmetry, 1995, 6, 2977; H. Kawakami, T. Ebata, K. Okano, K. Matsumoto, K. Koseki and H. Matsushita, Patent; Chem. Abstr., 1994, 120, 107640g.