Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-claisen rearrangement/oxa-6π electrocyclization strategy

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4795-4797

  Menz, Helge ^a   Kirsch, Stefan F ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750347225     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061856x     Document Type: Article

References (44)

1. For general reviews, see: (a) Kuthan, J.; Sebek, P.; Boehm, S. Adv. Heterocycl. Chem. 1995, 62, 19.
2. (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon: Oxford, UK, 1984; Vol. 3, p 737.
3. (a) Kluge, A. F.; Lillya, C. P. J. Am. Chem. Soc. 1971, 93, 4458.
4. (b) Kluge, A. F.; Lillya, C. P. J. Org. Chem. 1971, 36, 1977.
5. (c) Zhu, Y.; Ganapathy, S.; Liu, R. S. H. J. Org. Chem. 1992, 57, 1110.
6. For references pertinent to the stabilizing effect of substitution on the kinetic stability of monocyclic 2H-pyrans, see; (a) Duperrier, A.; Dreux, J. Tetrahedron Lett. 1970, 11, 3127.
7. (b) Marvell, E. N.; Gosink, T.; Churchley, P.; Li, T. H. J. Org. Chem. 1972, 37, 2989.
8. (c) Marvell, E. N.; Chadwick, T.; Caple, G.; Gosink, T.; Zimmer, G. J. Org. Chem. 1972, 37, 2992.
9. (d) Gosink, T. A. J. Org. Chem. 1974, 39, 1942.
10. (e) de Groot, A.; Jansen, B. J. M. Tetrahedron Lett. 1975, 16, 3407.
11. (f) Roedik, A.; Neukam, T. Liebigs Ann. Chem. 1975, 240.
12. (g) Moorhoff, C. M. Synthesis 1997, 685.
13. (h) Kouno, R.; Tsubota, T.; Okauchi, T.; Minami, T. J. Org. Chem. 2000, 65, 4326.
14. (a) Takanishi, K.; Urabe, H.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 2281.
15. (b) Adams, R. D.; Chen, L. J. Am. Chem. Soc. 1994, 116, 4467.
16. (c) Quing, F.-L.; Gao, W.-Z. Tetrahedron Lett. 2000, 41, 7727.
17. (d) Fan, M.; Yan, Z.; Liu, W.; Liang, Y. J. Org. Chem. 2005, 70, 8204.
18. For synthetic routes to bicyclic 2H-pyrans, see inter alia: (a) Shishido, K.; Shitara, E.; Fukumoto, K. J. Am. Chem. Soc. 1985, 107, 5810.
19. (b) Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570.
20. For selected references on electrocyclic ring-closures involving 1-oxatrienes, see: (a) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 23 and references cited herein.
21. (b) Shishido, K.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1986, 27, 971.
22. (c) Stevenson, R.; Weber, J. V. J. Nat. Prod. 1988, 51, 1215.
23. (d) Kurdyumov, A. V.; Hsung, R. P.; Ihlen, K.; Wang, J. Org. Lett. 2003, 5, 3935.
24. (e) Pujanauski, B. G.; Prasad, B. A. B.; Sarpong, R. J. Am. Chem. Soc. 2006, 128, 6786.
25. For leading references on electrocyclic ring-closures involving 1-azatrienes, see: (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763.
26. (b) Tanaka, K.; Mori, H.; Katsumura, S. J. Org. Chem. 2001, 66, 3099.
27. (a) Balaban, T.-S.; Balaban, A. T. Tetrahedron Lett. 1987, 28, 1341.
28. (b) Moorhoff, C. M. Tetrahedron 1997, 53, 2241.
29. (c) Moorhoff, C. M.; Winkler, D. New J. Chem. 1998, 1485.
30. For reaction with 2H-pyrans formed in situ, see: (a) Belosludtsev, Y. Y.; Borer, B. C.; Taylor, R. J. K. Synthesis 1991, 320.
31. (b) Obrecht, D. Helv. Chim. Acta 1991, 74, 27.
32. (c) Charoenying, P.; Davies, D. H.; McKerrecher, D.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 1913.
33. (d) Tius, M. A.; Hu, H.; Kawakami, J. K.; Busch-Petersen, J. J. Org. Chem. 1998, 63, 5971.
34. (e) Obrecht, D.; Zumbrunn, C.; Müller, K. J. Org. Chem. 1999, 64, 6182.
35. Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925.
36. During the course of this work, a gold(I)-catalyzed synthesis of enantioenriched dihydropyrans via chirality transfer utilizing a propargyl-Claisen rearrangement/6-endo-trig heterocyclization was reported. Our protocol gives racemic 2H-pyrans: Sherry, B. D.; Maus, L.; Laforteza, B. N.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 8132.
37. Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151.
38. For Ag(I)-catalyzed alkyne activation, see inter alia: (a) Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
39. (b) Grissom, J. W.; Kilingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603.
40. (c) Harrison, T. J.; Dake, G. R. Org. Lett. 2004, 6, 5023.
41. (d) Harrison, T. J.; Kozak, J. A.; Corbella-Pané, M.; Dake, G. R. J. Org. Chem. 2006, 71, 4525.
42. +)].
43. Zehnder, L. R.; Wie, L.; Hsung, R. P.; Cole, K. P.; McLaughlin, M. J.; Shen, H. C.; Skenicka, H. M.; Wang, J.; Zificsak, C. A. Org. Lett. 2001, 14, 2141.
44. 3-catalyzed addition of propargyl alcohols to 2-propynoic acid derivatives, see: Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241.