The First aza-Wittig Reaction Involving a non-Cumulated Sulfoxy Group

Synlett

Volumn , Issue 1, 2004, Pages 101-105

  Hemming, Karl ^a   Loukou, Christina ^a   Elkatip, Sinem ^b   Smalley, Robert K ^c  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

^b CITY UNIVERSITY OF NEW YORK   (United States)

^c UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

1,3 dipolar cycloadditions; 2,1 benzothiazine; Aza Wittig reaction; Sulfimide; Sulfoxides

Indexed keywords

2 AZIDOBENZONITRILE OXIDE; AZIDE; BENZOTHIAZINE DERIVATIVE; NITRILE; PHOSPHORANE DERIVATIVE; SULFOXIDE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; REACTION ANALYSIS; RING CLOSING METATHESIS; STAUDINGER REACTION; SYNTHESIS; WITTIG REACTION;

EID: 0346970813     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43352     Document Type: Article

References (61)

1. For reviews, see: (a) Wamhoff, H.; Richardt, G.; Stölben, S. Adv. Heterocycl. Chem. 1995, 159. (b) Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 211. (c) Molina, P.; Viliplana, M. J. Synthesis 1994, 1197.
2. For reviews, see: (a) Wamhoff, H.; Richardt, G.; Stölben, S. Adv. Heterocycl. Chem. 1995, 159. (b) Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 211. (c) Molina, P.; Viliplana, M. J. Synthesis 1994, 1197.
3. For reviews, see: (a) Wamhoff, H.; Richardt, G.; Stölben, S. Adv. Heterocycl. Chem. 1995, 159. (b) Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 211. (c) Molina, P.; Viliplana, M. J. Synthesis 1994, 1197.
4. For reviews, see: (a) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. (b) Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981,37, 437.
5. For reviews, see: (a) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. (b) Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981,37, 437.
6. (3) See, for example: (a) Charette, A. B.; Boezio, A. A.; Janes, M. K. Org. Lett. 2000, 2, 3777. (b) Hemming, K.; Bevan, M. J.; Loukou, C.; Patel, S. D.; Renaudeau, D. Synlett 2000, 1565.
7. See, for example: (a) Charette, A. B.; Boezio, A. A.; Janes, M. K. Org. Lett. 2000, 2, 3777. (b) Hemming, K.; Bevan, M. J.; Loukou, C.; Patel, S. D.; Renaudeau, D. Synlett 2000, 1565.
8. See, for example: (a) Eguchi, S.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) O'Neil, I. A.; Thompson, S.; Murray, C. L. ; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787. (c) Anwar, B.; Grimsey, P.; Hemming, K.; Karajniewski, M.; Loukou, C. Tetrahedron Lett. 2000, 41, 10107.
9. See, for example: (a) Eguchi, S.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) O'Neil, I. A.; Thompson, S.; Murray, C. L. ; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787. (c) Anwar, B.; Grimsey, P.; Hemming, K.; Karajniewski, M.; Loukou, C. Tetrahedron Lett. 2000, 41, 10107.
10. See, for example: (a) Eguchi, S.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) O'Neil, I. A.; Thompson, S.; Murray, C. L. ; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787. (c) Anwar, B.; Grimsey, P.; Hemming, K.; Karajniewski, M.; Loukou, C. Tetrahedron Lett. 2000, 41, 10107.
11. Staudinger, H.; Hauser, E. Helv. Chim. Acta 1921, 4, 861.
12. For a review, see: Johnson, C. R. In Comprehensive Organic Chemistry, Vol 3; Barton, D. H. R.; Ollis, W. D., Eds.; Pergamon: New York, 1979, Chap. 11.10, 215.
13. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
14. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
15. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
16. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
17. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
18. See, for example: (a) Tarbell, D. S.; Weaver, C. J. Am. Chem. Soc. 1941, 63, 2939. (b) Varkey, T. E.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1974, 39, 3365; and references cited therein, (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemura, S. Chirality 2000, 12, 299. (d) Cram, D. J.; Day, J.; Rayner, D. R. ; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369. (e) Johnson, C. R.; Rigau, J. J. J. Org. Chem. 1968, 33, 4340. (f) Kise, H.; Whitfield, G. F.; Swern, D. J. Org. Chem. 1972, 37, 1121.
19. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
20. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
21. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
22. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
23. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
24. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
25. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
26. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
27. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
28. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
29. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
30. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
31. See, for example: (a) Mann, F. G.; Pope, W. J. J. Chem. Soc. 1922, 1052. (b) For a review, see: Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. (c) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Chem. Commun. 2001, 1256. (d) Shiraishi, Y.; Naito, T.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2002, 41, 4376. (e) Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065. (f) Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. (g) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937. (h) Hayashi, Y.; Swern, D. J. Am. Chem. Soc. 1973, 95, 5205. (i) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301. (j) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (k) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (l) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2002, 85, 3773. (m) Armstrong, A.; Cooke, R. S. Chem. Commun. 2002, 904.
32. (a) For a review, see: Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (b) Jones, S. D.; Kennewell, P. D.; Tulley, W. R.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 447. (c) Harmata, M.; Claassen, R. J. II.; Barnes, C. L. J. Org. Chem. 1991, 56, 5059.
33. (a) For a review, see: Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (b) Jones, S. D.; Kennewell, P. D.; Tulley, W. R.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 447. (c) Harmata, M.; Claassen, R. J. II.; Barnes, C. L. J. Org. Chem. 1991, 56, 5059.
34. (a) For a review, see: Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (b) Jones, S. D.; Kennewell, P. D.; Tulley, W. R.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 447. (c) Harmata, M.; Claassen, R. J. II.; Barnes, C. L. J. Org. Chem. 1991, 56, 5059.
35. (a) Hori, M.; Kataoka, T.; Shimizu, H.; Matsua, K. Tetrahedron Lett. 1979, 20, 3969.
36. (b) Shimizu, H.; Ikedo, K.; Hamada, K.; Matsumoto, H.; Ozawa, M.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1990, 31, 7021.
37. (c) Shimizu, H.; Hamada, K.; Ozawa, M.; Kataoka, T.; Hori, M.; Kobayashi, K.; Tuda, Y. Tetrahedron Lett. 1991, 32, 4359.
38. (d) Shimizu, H.; Ikedo, K.; Hamada, K.; Ozawa, M.; Matsumoto, H.; Kamata, K.; Nakamuru, H.; Ji, M.; Kataoka, T.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1991, 1733.
39. (e) Grant, R. D.; Moody, C. J.; Rees, C. W.; Tsoi, S. C. J. Chem. Soc., Chem. Commun. 1982, 884.
40. (f) Moody, C. J.; Rees, C. W.; Tsoi, S. C.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1981, 927.
41. (g) Gairns, R. S.; Grant, R. D.; Moody, C. J.; Rees, C. W.; Tsoi, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 483.
42. Gilchrist, T. L.; Rees, C. W.; Vaughan, D. J. Chem. Soc., Chem. Commun. 1978, 1049; and references cited therein.
43. Bludssus, W.; Mews, R. J. Chem. Soc., Chem. Commun. 1978, 35.
44. Rees, C. W.; Yue, T.-Y. Chem. Commun. 1998, 1207.
45. (a) Strekowski, L.; Henary, M.; Kim, N.; Michniak, B. B. Bioorg. Med. Chem. Lett. 1999, 9, 1033.
46. (b) Popova, T. V.; Denisov, A. Y.; Shakirov, M. M.; Komarova, N. I.; Alekseyev, P. V.; Serebriakova, M. V.; Godovikova, T. S. J. Photochem. Photobiol., B 2001, 61, 68.
47. For a review, see: Reggelin, M.; Zur, C. Synthesis 2000, 1.
48. (a) Kresze, G.; Wucherpfennig, W. Angew. Chem., Int. Ed. Engl. 1967, 6, 149.
49. (b) For a review, see: Weinreb, S. M. Acc. Chem. Res. 1988, 21, 313.
50. Azadi-Ardakani, M.; Smalley, R. K.; Smith, R. H. J. Chem. Soc., Perkin Trans. 1 1983, 2501.
51. (a) L'Abbe, G. Ind. Chim. Belg. 1971, 36, 3.
52. (b) L'Abbe, G. Ind. Chim. Belg. 1969, 34, 519.
53. (c) L'Abbe, G.; Hassner, A. J. Heterocycl. Chem. 1970, 7, 361.
54. (d) L'Abbe, G.; Mathys, G.; Toppet, S. J. Org. Chem. 1975, 40, 1549.
55. (e) Bourgois, J.; Bourgois, M.; Texier, T. Bull. Soc. Chim. Fr. 1978, 485.
56. Purwono, B.; Smalley, R. K.; Porter, T. C. Synlett 1992, 231.
57. 2S requires MH 401.1072.
58. + 635.1922.
59. + 357.1056.
60. 2S requires MH 375.1167.
61. Luheshi, A.-B. N.; Salem, S. M.; Smalley, R. K.; Kennewell, P. D.; Westwood, R. Tetrahedron Lett. 1990, 31, 6561.