Stereoselective synthesis of cyclic ethers using vinylogous sulfonates as radical acceptors: Effect of E/Z geometry and temperature on diastereoselectivity

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4523-4528

  Evans, P Andrew ^a   Manangan, Thara ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; ETHER DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; ETHERS, CYCLIC; KINETICS; STEREOISOMERISM; SULFONIC ACIDS; TEMPERATURE; VINYL COMPOUNDS;

EID: 0034725822     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991970b     Document Type: Article

References (54)

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19. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
20. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
21. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
22. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
23. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
24. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
25. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
26. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
27. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
28. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
29. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
30. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
31. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
32. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
33. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
34. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
35. For some representative examples of cyclic ethers construction using intramolecular radical cyclizations, see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32. 1491. (e) Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313. (g) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837. (h) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (i) Dulcère, J.-P.; Dumez, E.; Faure, R. J. Chem. Soc., Chem. Commun. 1995, 897. (j) Maiti, G.; Adhikari, S.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1995, 927. (k) Srikrishna, A.; Viswajanani, R.; Yelamaggad, C. V. Tetrahedron Lett. 1995, 36, 1127. (l) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (m) Lee, E.; Park, C.-P.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017. (o) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1996, 61, 677. (p) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157. (q) Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144. (i) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811 and pertinent references therein.
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50. For the early development of this reaction, see: (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829. (b) Keck, G. E.; Yates, J. B. J. Org. Chem. 1982, 47, 3590.
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53. The LUMO of a vinyl sulfone and a vinyl ether are known to have larger coefficients at the β- and α-carbons, respectively, thus reinforcing each other in α-alkoxy vinyl sulfone. See: (a) Sims, J.; Houk, K. N. J. Am. Chem. Soc. 1973, 95, 5798. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley and Sons: New York, 1977; p 186.
54. The LUMO of a vinyl sulfone and a vinyl ether are known to have larger coefficients at the β- and α-carbons, respectively, thus reinforcing each other in α-alkoxy vinyl sulfone. See: (a) Sims, J.; Houk, K. N. J. Am. Chem. Soc. 1973, 95, 5798. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley and Sons: New York, 1977; p 186.