Reversing the polarity of enol ethers: An anodic route to tetrahydrofuran and tetrahydropyran rings [1]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5636-5637

  Sutterer, Angela ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHANOL; METHYL DERIVATIVE; SCAVENGER; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS ISOMER; CYCLIZATION; ELECTROLYSIS; LETTER; OXIDATION; POLARIMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; TRANS ISOMER;

EID: 0034647199     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001063k     Document Type: Letter

References (23)

1. For recent references see: (a) Frey, D. A.; Reddy, S. H. K.; Moeller, K. D. J. Org. Chem. 1999, 64, 2805. (b) Reddy, S. H. K.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 8027. For a review see: (c) Moeller, K. D. Top. Curr. Chem. 1997, 185, 49.
2. For recent references see: (a) Frey, D. A.; Reddy, S. H. K.; Moeller, K. D. J. Org. Chem. 1999, 64, 2805. (b) Reddy, S. H. K.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 8027. For a review see: (c) Moeller, K. D. Top. Curr. Chem. 1997, 185, 49.
3. For recent references see: (a) Frey, D. A.; Reddy, S. H. K.; Moeller, K. D. J. Org. Chem. 1999, 64, 2805. (b) Reddy, S. H. K.; Moeller, K. D. Tetrahedron Lett. 1998, 39, 8027. For a review see: (c) Moeller, K. D. Top. Curr. Chem. 1997, 185, 49.
4. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
5. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
6. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
7. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
8. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
9. For a review see: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175. For recent methodology involving the synthesis of furans and pyrans: (b) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461. (c) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092. (d) Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842. (f) Crich, D.; Huang, X.; Newcomb. M. Org. Lett. 1999, 1, 225.
10. Hudson, C. M.; Moeller, K. D. J. Am. Chem. Soc. 1994, 116, 3347.
11. The substrates were synthesized using a Wittig reaction on the corresponding lactol. Moeller, K. D.; Tinao, L. V. J. Am. Chem. Soc. 1992, 114, 1033.
12. For a complementary approach to furans using a Wittig reaction followed by a Michael reaction see: (a) Georges, M.; Tam, T. F.; Fraiser-Reid, B. J. Org. Chem. 1985, 50, 5754. (b) Bloch, R.; Seek, M. Tetrahedron 1989, 45, 3731.
13. For a complementary approach to furans using a Wittig reaction followed by a Michael reaction see: (a) Georges, M.; Tam, T. F.; Fraiser- Reid, B. J. Org. Chem. 1985, 50, 5754. (b) Bloch, R.; Seek, M. Tetrahedron 1989, 45, 3731.
14. A 100 PPI electrode was used (available from The Electrosynthesis Co., Inc.). The preparative electrolyses were conducted utilizing a Model 630 coulometer, a Model 410 potentiostatic controller, and a Model 420A power supply purchased from the Electrosynthesis Co., Inc.
15. The yield of 2c was determined by proton NMR using an internal standard due to the volatility of the product. All of the other yields reported represent the amount of pure product isolated from the reaction.
16. For an example of an enol ether radical cation derived cyclization under kinetic control see ref 1a.
17. For an example of an enol ether radical cation derived cyclization under thermodynamic control see ref 3.
18. New, D. G.; Tesfai, Z.; Moeller, K. D. J. Org. Chem. 1996, 61, 1578.
19. Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372.
20. Tinao-Wooldndge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 59, 2381.
21. These reactions did not require the use of 2,6-lulidine as a proton scavanger.
22. For a mechanism see: Yoshida, J. Top. Curr. Chem. 1994, 170, 39.
23. Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317.