Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4449-4456

  Bergmeier, Stephen C ^a   Stanchina, Dionne M ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000890629     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970473x     Document Type: Article

References (89)

1. (a) Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. J. Antibiotics 1976, 29, 97.
2. (b) Abe, F.; Shibuya, K.; Ashizawa, J.; Takahashi, K.; Horinishi, H.; Matsuda, A.; Ishizuka, M.; Takeushi, T.; Umezawa, H. J. Antibiot. 1985, 38, 411.
3. For some representative syntheses, see: (c) Fuji, K.; Kawabata, T.; Diryu, Y.; Sugiura, Y. Heterocycles 1996, 42, 701. Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957. (e) Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Ito, Y.; Terashima, S. Chem. Lett. 1990, 723. (f) Pearson, W. H.; Hines, J. V. J. Org. Chem. 1989, 54, 4235.
4. For some representative syntheses, see: (c) Fuji, K.; Kawabata, T.; Diryu, Y.; Sugiura, Y. Heterocycles 1996, 42, 701. Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957. (e) Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Ito, Y.; Terashima, S. Chem. Lett. 1990, 723. (f) Pearson, W. H.; Hines, J. V. J. Org. Chem. 1989, 54, 4235.
5. For some representative syntheses, see: (c) Fuji, K.; Kawabata, T.; Diryu, Y.; Sugiura, Y. Heterocycles 1996, 42, 701. Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957. (e) Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Ito, Y.; Terashima, S. Chem. Lett. 1990, 723. (f) Pearson, W. H.; Hines, J. V. J. Org. Chem. 1989, 54, 4235.
6. For some representative syntheses, see: (c) Fuji, K.; Kawabata, T.; Diryu, Y.; Sugiura, Y. Heterocycles 1996, 42, 701. Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957. (e) Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Ito, Y.; Terashima, S. Chem. Lett. 1990, 723. (f) Pearson, W. H.; Hines, J. V. J. Org. Chem. 1989, 54, 4235.
7. (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-363 and references therein.
8. (b) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037-3040.
9. For information on isolation and structure determination of balanol, see: (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453. Synthesis: (b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. (e) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
10. For information on isolation and structure determination of balanol, see: (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453. Synthesis: (b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. (e) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
11. For information on isolation and structure determination of balanol, see: (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453. Synthesis: (b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. (e) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
12. For information on isolation and structure determination of balanol, see: (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453. Synthesis: (b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. (e) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
13. For information on isolation and structure determination of balanol, see: (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453. Synthesis: (b) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148. (e) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
14. (a) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274.
15. (b) Barrett, A. G. M.; Seefeld, M. A. J. Chem. Soc., Chem. Commun. 1993, 339-341.
16. (c) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164.
17. (d) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1991, 30 (12), 1531-1750.
18. (a) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730-732.
19. While the intramolecular cyclization of an azidoformate with an olefin is rare, the intermolecular insertion reaction between the nitrene and C-4 has been exploited to some advantage. See: (a) Lwowski, W.: Carbonylnitrenes In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 185-224. (b) Edwards, O. E. Acylnitrene Cyclizations. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 225-304. Lwowski, W.: Acyl Azides and Nitrene. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; pp 205-246. Lwowski, W. Nitrenes. React. Intermed. 1985, 3, 305-332.
20. While the intramolecular cyclization of an azidoformate with an olefin is rare, the intermolecular insertion reaction between the nitrene and C-4 has been exploited to some advantage. See: (a) Lwowski, W.: Carbonylnitrenes In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 185-224. (b) Edwards, O. E. Acylnitrene Cyclizations. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 225-304. Lwowski, W.: Acyl Azides and Nitrene. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; pp 205-246. Lwowski, W. Nitrenes. React. Intermed. 1985, 3, 305-332.
21. While the intramolecular cyclization of an azidoformate with an olefin is rare, the intermolecular insertion reaction between the nitrene and C-4 has been exploited to some advantage. See: (a) Lwowski, W.: Carbonylnitrenes In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 185-224. (b) Edwards, O. E. Acylnitrene Cyclizations. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 225-304. Lwowski, W.: Acyl Azides and Nitrene. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; pp 205-246. Lwowski, W. Nitrenes. React. Intermed. 1985, 3, 305-332.
22. While the intramolecular cyclization of an azidoformate with an olefin is rare, the intermolecular insertion reaction between the nitrene and C-4 has been exploited to some advantage. See: (a) Lwowski, W.: Carbonylnitrenes In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 185-224. (b) Edwards, O. E. Acylnitrene Cyclizations. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp 225-304. Lwowski, W.: Acyl Azides and Nitrene. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; pp 205-246. Lwowski, W. Nitrenes. React. Intermed. 1985, 3, 305-332.
23. Deroose, F. D.; De Clercq, P. J. J. Org. Chem. 1995, 60, 321-330.
24. (a) Lwowski, W.; Mattingly, T. W., Jr. J. Am. Chem. Soc. 1965, 87, 1947-1958.
25. (b) Lwowski, W. Acyl Azides and Nitrene. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; pp 231-235.
26. Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360-5364.
27. Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533-4536.
28. Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1101-1133.
29. 4, and acid scavengers such as poly(4-vinylpyridine) and 1,8-bis(dimethylamino)-naphthalene (Proton Sponge) were used to preclude the formation of HCl. We did not observe aziridine formation when any of these agents were used. Only oxazolidinones were obtained in low yield with the exception of the case of the Proton Sponge where only polymeric material was formed.
30. The predominance of the trans isomer can be rationalized by a chair-like transition state as discussed in our earlier work. See ref 10.
31. Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, Chapter 12, pp 277-406.
32. Although the products are not as well characterized, heating in toluene or decane also gives only products consistent with nitrenes reacting with the solvent, (a) Anderson, D. J.; Horwell. D. C.; Stanton, E.; Gilchrist, T. L.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1972, 1317-1320. (b) Colonna, S.; Stirling, C. J. J. Chem. Soc., Perkin Trans. 1 1974, 2120-2122. Atkinson, R. S. Azides and Nitrenes Attached to Elements Other than Carbon. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; p 280. Horner, L.; Christmann, A. Chem. Ber. 1963, 388-398. (e) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
33. Although the products are not as well characterized, heating in toluene or decane also gives only products consistent with nitrenes reacting with the solvent, (a) Anderson, D. J.; Horwell. D. C.; Stanton, E.; Gilchrist, T. L.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1972, 1317-1320. (b) Colonna, S.; Stirling, C. J. J. Chem. Soc., Perkin Trans. 1 1974, 2120-2122. Atkinson, R. S. Azides and Nitrenes Attached to Elements Other than Carbon. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; p 280. Horner, L.; Christmann, A. Chem. Ber. 1963, 388-398. (e) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
34. Although the products are not as well characterized, heating in toluene or decane also gives only products consistent with nitrenes reacting with the solvent, (a) Anderson, D. J.; Horwell. D. C.; Stanton, E.; Gilchrist, T. L.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1972, 1317-1320. (b) Colonna, S.; Stirling, C. J. J. Chem. Soc., Perkin Trans. 1 1974, 2120-2122. Atkinson, R. S. Azides and Nitrenes Attached to Elements Other than Carbon. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; p 280. Horner, L.; Christmann, A. Chem. Ber. 1963, 388-398. (e) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
35. Although the products are not as well characterized, heating in toluene or decane also gives only products consistent with nitrenes reacting with the solvent, (a) Anderson, D. J.; Horwell. D. C.; Stanton, E.; Gilchrist, T. L.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1972, 1317-1320. (b) Colonna, S.; Stirling, C. J. J. Chem. Soc., Perkin Trans. 1 1974, 2120-2122. Atkinson, R. S. Azides and Nitrenes Attached to Elements Other than Carbon. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; p 280. Horner, L.; Christmann, A. Chem. Ber. 1963, 388-398. (e) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
36. Although the products are not as well characterized, heating in toluene or decane also gives only products consistent with nitrenes reacting with the solvent, (a) Anderson, D. J.; Horwell. D. C.; Stanton, E.; Gilchrist, T. L.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1972, 1317-1320. (b) Colonna, S.; Stirling, C. J. J. Chem. Soc., Perkin Trans. 1 1974, 2120-2122. Atkinson, R. S. Azides and Nitrenes Attached to Elements Other than Carbon. In Azides and Nitrenes; Scriven, E., Ed.; Academic: Orlando, 1984; p 280. Horner, L.; Christmann, A. Chem. Ber. 1963, 388-398. (e) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
37. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc, 1993, 115, 5328.
38. (b) Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
39. (a) Kogami, Y.; Okawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 2963.
40. (b) Stamm, H.; Speth, D. Arch. Pharm. (Weinheim, Ger.) 1989, 322, 277.
41. (c) Pirrung, M. C.; Nunn, D. S. Bioorg. Med. Chem. Lett. 1992, 2, 1489.
42. (d) Ho, M.; Chung, J. K. K.; Tang, N. Tetrahedron Lett. 1993, 34, 6513.
43. Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
44. (a) Takeuchi, H.; Koyama, K. J. Chem. Soc., Perkin Trans. 2 1981, 121.
45. (b) Jones, D. S.; Srinivasan, A.; Kasina, S.; Fritzberg, A. R.; Wilkening, D. W. J. Org. Chem. 1989, 54, 1940.
46. (c) Kim, N.-S.; Rang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489.
47. (d) Legters, J.; Willems, J. G. H.; Thijs, L.; Zwanenburg, B. Reel. Trav. Chim. Pays-Bas 1992, 111, 59.
48. (a) De Kimpe, N.; Boelens, M.; Contreras, J. Tetrahedron Lett. 1996, 37, 3171-3174.
49. (b) Kim, D.-K.; Kim, G.; Kim, Y. W. J. Chem. Soc., Perkin Trans. 1 1996, 803-808.
50. (c) Armstrong, R. W.; Moran, E. J. J. Am. Chem. Soc. 1992, 371-372.
51. (d) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1994, 35, 2207-2210.
52. (a) Lin, P.-Y.; Bellos, K.; Stamm, H.; Onistschemko, A. Tetrahedron, 1992, 48, 2359-2372.
53. (b) Carreaux, F.; Dureault, A.; Depezey, J. C. Synlett 1992, 527.
54. (c) Voronkov, M. G.; Knutov, V. I.; Shevko, O. N. J. Gen. Chem. USSR 1992, 5, 704.
55. (d) Hashimoto, H.; Shimada, K.; Horito, S. Tetrahedron Lett. 1993, 34, 4953 -4956.
56. (e) Osborn, H. M. J.; Sweeney, J. B.; Howson, B. Synlett 1994, 145.
57. (f) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S. Tetrahedron Lett. 1994, 35, 2207-2210.
58. (a) Gutherie, R. D.; Williams, G. J. J. Chem. Soc., Perkin Trans. 1 1976, 801-804.
59. 3, see: Brandstrom, A.; Lamm, B.; Palmerlz, I. Acta Chem. Scand. B 1974, 28, 699-701. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035-13050. Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891-892.
60. 3, see: Brandstrom, A.; Lamm, B.; Palmerlz, I. Acta Chem. Scand. B 1974, 28, 699-701. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035-13050. Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891-892.
61. 3, see: Brandstrom, A.; Lamm, B.; Palmerlz, I. Acta Chem. Scand. B 1974, 28, 699-701. Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035-13050. Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891-892.
62. Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 67, 2488-2496.
63. For examples of opening activated aziridines with iodide, see: (a) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906. (b) Nadir, U. K.; Basu, N. Tetrahedron Lett. 1992, 33, 7903-7906. For examples of opening of activated aziridines with bromide, see: (c) Dureault, A.; Tranchepain, I.; Depezay, J. C. J. Org. Chem. 1989, 54, 5324-5330. For examples of opening of aziridines with chloride, see: (d) Kyburz, E.; Els, H.; Majnoni, S.; Englert, G.; von Planta, C.; Furst, A.; Plattner, P. A. Helv. Chim. Acta 1966, 49, 359. (e) Gurjar, M. K.; Patil, V. J.; Yadav, J. S.; Rama Rao, A. V. Carbohydr. Res. 1984, 129, 267.
64. For examples of opening activated aziridines with iodide, see: (a) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906. (b) Nadir, U. K.; Basu, N. Tetrahedron Lett. 1992, 33, 7903-7906. For examples of opening of activated aziridines with bromide, see: (c) Dureault, A.; Tranchepain, I.; Depezay, J. C. J. Org. Chem. 1989, 54, 5324-5330. For examples of opening of aziridines with chloride, see: (d) Kyburz, E.; Els, H.; Majnoni, S.; Englert, G.; von Planta, C.; Furst, A.; Plattner, P. A. Helv. Chim. Acta 1966, 49, 359. (e) Gurjar, M. K.; Patil, V. J.; Yadav, J. S.; Rama Rao, A. V. Carbohydr. Res. 1984, 129, 267.
65. For examples of opening activated aziridines with iodide, see: (a) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906. (b) Nadir, U. K.; Basu, N. Tetrahedron Lett. 1992, 33, 7903-7906. For examples of opening of activated aziridines with bromide, see: (c) Dureault, A.; Tranchepain, I.; Depezay, J. C. J. Org. Chem. 1989, 54, 5324-5330. For examples of opening of aziridines with chloride, see: (d) Kyburz, E.; Els, H.; Majnoni, S.; Englert, G.; von Planta, C.; Furst, A.; Plattner, P. A. Helv. Chim. Acta 1966, 49, 359. (e) Gurjar, M. K.; Patil, V. J.; Yadav, J. S.; Rama Rao, A. V. Carbohydr. Res. 1984, 129, 267.
66. For examples of opening activated aziridines with iodide, see: (a) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906. (b) Nadir, U. K.; Basu, N. Tetrahedron Lett. 1992, 33, 7903-7906. For examples of opening of activated aziridines with bromide, see: (c) Dureault, A.; Tranchepain, I.; Depezay, J. C. J. Org. Chem. 1989, 54, 5324-5330. For examples of opening of aziridines with chloride, see: (d) Kyburz, E.; Els, H.; Majnoni, S.; Englert, G.; von Planta, C.; Furst, A.; Plattner, P. A. Helv. Chim. Acta 1966, 49, 359. (e) Gurjar, M. K.; Patil, V. J.; Yadav, J. S.; Rama Rao, A. V. Carbohydr. Res. 1984, 129, 267.
67. For examples of opening activated aziridines with iodide, see: (a) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903-1906. (b) Nadir, U. K.; Basu, N. Tetrahedron Lett. 1992, 33, 7903-7906. For examples of opening of activated aziridines with bromide, see: (c) Dureault, A.; Tranchepain, I.; Depezay, J. C. J. Org. Chem. 1989, 54, 5324-5330. For examples of opening of aziridines with chloride, see: (d) Kyburz, E.; Els, H.; Majnoni, S.; Englert, G.; von Planta, C.; Furst, A.; Plattner, P. A. Helv. Chim. Acta 1966, 49, 359. (e) Gurjar, M. K.; Patil, V. J.; Yadav, J. S.; Rama Rao, A. V. Carbohydr. Res. 1984, 129, 267.
68. (a) Dureault, A.; Tranchepain, I.; Depezay, J-C. J. Org. Chem. 1989, 54, 5324-5330.
69. (b) Baldwin, J. E.; Adlington, R. M.; O'Neil, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852-1854.
70. (c) Baldwin, J. E.; Farthing, C. N.; Russell, A. T.; Schofield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761-3764.
71. (d) Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745-3746.
72. (e) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis, 1996, 333-335.
73. (f) Chakraborty, T. K.; Gangakhedkar, K. Tetrahedron Lett. 1991, 32, 1897-1898.
74. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185-4188.
75. (a) Yi, F.; Wang, T.; Izawa, S.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465-6466.
76. (b) Hirama, M.; Nishizaki, I.; Shigemoto, T.; Ito, S. J. Chem. Soc., Chem. Commun. 1986, 393-394.
77. (c) Bartlett, P. A.; Tauzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619-622.
78. Dyen, M. E.; Swern, D. Chem. Rev. 1967, 67, 197.
79. Kemp, S. J.; Jianming, B.; Pedersen, S. F. J. Org. Chem. 1996, 61, 7162-7167.
80. (a) Skell, P. S.; Woodworth, R. C. J. Am. Chem. Soc. 1956, 78, 4496.
81. (b) Woodworth, R. C.; Skell, P. S. J. Am. Chem. Soc. 1959, 81, 3384.
82. (a) McConaghy, J. S., Jr.; Lwowski, W. J. Am. Chem. Soc. 1967, 89, 2357.
83. (b) McConaghy, J. S., Jr.; Lwowski, W. J. Am. Chem. Soc. 1967, 89, 4450.
84. (c) Mishra, A.; Rice, S. N.; Lwowski, W. J. Org. Chem. 1968, 33, 481.
85. Kauffman, G. B.; Teter, L. A. Inorg. Synth. 1961, 7, 9-12.
86. Still, C. W.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 50, 2923.
87. Vorbruggen, H.; Krolikiewicz, K. Collect. Czech. Chem. Commun. 1979, 35.
88. Vittorelli, P.; Peter-Katalinic, J.; Mukherjee-Muller, G.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1975, 58, 1379-1425.
89. Takano, S.; Nishizawa, S.; Akiyama, M.; Ogasawara, K. Heterocycles 1984, 22, 1779-1788.