Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides

Tetrahedron

Volumn 54, Issue 12, 1998, Pages 2709-2722

  Kotsuki, Hiyoshizo ^a   Shimanouchi, Tomoyasu ^a   Ohshima, Reiji ^a   Fujiwara, Shunsuke ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; HALIDE; LITHIUM CHLORIDE; LITHIUM DERIVATIVE; SILICA GEL;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032546288     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83007-X     Document Type: Article

References (90)

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12. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
13. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
14. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
15. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
16. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
17. For some examples using silica gel as the acid catalyst, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, Jr., W. F.; Jones, III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146-4152 and the references cited therein. See also: Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825-3828; de la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa F. ibid. 1996, 37, 1113-1116; Patil, V. J.; Mävers, U. ibid. 1996, 37, 1281-1284; Pérez, J. M.; López-Alvarado, P.; Alonso, M. Á.; Avendaño, C.; Menéndez, J. C. ibid. 1996, 37, 6955-6958; Matsumoto, Y.; Mita, K.; Hashimoto, K.; Iio, H.; Tokoroyama, T. Tetrahedron 1996, 52, 9387-9398.
18. a) Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159-2162.
19. b) Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H, J. Org. Chem. 1996, 61, 984-990. See also: Raubo, P.; Wicha, J. Synlett 1993, 25-26; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703-704; Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583-7586.
20. b) Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H, J. Org. Chem. 1996, 61, 984-990. See also: Raubo, P.; Wicha, J. Synlett 1993, 25-26; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703-704; Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583-7586.
21. b) Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H, J. Org. Chem. 1996, 61, 984-990. See also: Raubo, P.; Wicha, J. Synlett 1993, 25-26; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703-704; Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583-7586.
22. b) Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H, J. Org. Chem. 1996, 61, 984-990. See also: Raubo, P.; Wicha, J. Synlett 1993, 25-26; Bennett, F.; Patel, N. M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703-704; Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583-7586.
23. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
24. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
25. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
26. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
27. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
28. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799; Buchanan, J. G.; Sable, H. Z. Selective Organic Transformations; Thyagarajan, B. S., Ed,; Wiley, 1972; Vol. 2, pp 1-95; Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367; Smith, J. G. Synthesis 1984, 629-656; Pfenninger, A. Synthesis 1986, 89-116; Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
29. Review: Bonini, C.; Righi, G. Synthesis 1994, 225-238. See also, Larock, R. C. Comprehensive Organic Transformations, VCH, New York, 1989; pp 508-509.
30. Review: Bonini, C.; Righi, G. Synthesis 1994, 225-238. See also, Larock, R. C. Comprehensive Organic Transformations, VCH, New York, 1989; pp 508-509.
31. For the use of LiX as a halide source for the preparation of β-halohydrins, see: a) Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061-2064. b) Ciaccio, J. A.; Addess, K. J.; Bell, T. W. ibid. 1986, 27, 3697-3700. c) Bajwa, J. S.; Anderson, R. C. ibid. 1991, 32, 3021-3024. d) Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250, e) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805-3812.
32. For the use of LiX as a halide source for the preparation of β-halohydrins, see: a) Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061-2064. b) Ciaccio, J. A.; Addess, K. J.; Bell, T. W. ibid. 1986, 27, 3697-3700. c) Bajwa, J. S.; Anderson, R. C. ibid. 1991, 32, 3021-3024. d) Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250, e) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805-3812.
33. For the use of LiX as a halide source for the preparation of β-halohydrins, see: a) Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061-2064. b) Ciaccio, J. A.; Addess, K. J.; Bell, T. W. ibid. 1986, 27, 3697-3700. c) Bajwa, J. S.; Anderson, R. C. ibid. 1991, 32, 3021-3024. d) Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250, e) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805-3812.
34. For the use of LiX as a halide source for the preparation of β-halohydrins, see: a) Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061-2064. b) Ciaccio, J. A.; Addess, K. J.; Bell, T. W. ibid. 1986, 27, 3697-3700. c) Bajwa, J. S.; Anderson, R. C. ibid. 1991, 32, 3021-3024. d) Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250, e) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805-3812.
35. For the use of LiX as a halide source for the preparation of β-halohydrins, see: a) Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061-2064. b) Ciaccio, J. A.; Addess, K. J.; Bell, T. W. ibid. 1986, 27, 3697-3700. c) Bajwa, J. S.; Anderson, R. C. ibid. 1991, 32, 3021-3024. d) Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250, e) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805-3812.
36. 2 was reported: Iranpoor, N.; Tarrian, T.; Movahedi, Z. Synthesis 1996, 1473-1476.
37. 2 was reported: Iranpoor, N.; Tarrian, T.; Movahedi, Z. Synthesis 1996, 1473-1476.
38. Wakogel C-300 (200-300 mesh) was used throughout this study. No significant differencies in reactivity were observed for other types of commercial-grade chromatography silica gel.
39. 4 380.0623, found 380.0593.
40. The addition of an equivalent amount of water to the salts gave somewhat better results. For example, KBr (72 h): 2b (36%), the hydrolyzed diol (3%), and 61% recovery; NaBr (72 h): 2b (45%). the hydrolyzed diol (4%), and 51% recovery; CsBr (72 h): 2b (45%), the hydrolyzed diol (4%), and 51% recovery.
41. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th Ed., Wiley-Interscience, New York, 1988; p 124.
42. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
43. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
44. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
45. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
46. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
47. For a similar finding, see: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1982, 935-938. The silica surface also exerts an extraordinarily "polar" effect on some organic transformations: Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773; Leffler, J. E.; Barbas. J. T.; Flowers, G. C. J. Org. Chem. 1982, 47, 2286-2287; Lindley, S. M.; Flowers, G. C.; Leffler, J. E. ibid. 1985, 50, 607-610; Spange, S.; Keutel, D.; Simon, F. J. Chim. Phys. 1992, 89, 1615-1622. For a review of the surface structure of silica gel, see: Knözinger, H. In The Hydrogen Bond. III. Dynamics, Thermodynamics and Special Systems, Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland, Amsterdam, 1976; Chapter 27.
48. For a similar finding, see: Oriaka, M.; Sugita, K.; Izumi, Y. J. Org. Chem. 1989, 54, 1116-1123.
49. Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693-1700; Magnusson, G.; Thorén, S. J. Org. Chem. 1973, 38, 1380-1384. See also: Rao, T. B.; Rao, J. M. Synth. Commun. 1993, 25, 1527-1533. No detectable amount of hexadecanal was observed in the crude mixture.
50. Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693-1700; Magnusson, G.; Thorén, S. J. Org. Chem. 1973, 38, 1380-1384. See also: Rao, T. B.; Rao, J. M. Synth. Commun. 1993, 25, 1527-1533. No detectable amount of hexadecanal was observed in the crude mixture.
51. Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693-1700; Magnusson, G.; Thorén, S. J. Org. Chem. 1973, 38, 1380-1384. See also: Rao, T. B.; Rao, J. M. Synth. Commun. 1993, 25, 1527-1533. No detectable amount of hexadecanal was observed in the crude mixture.
52. 16 of 7 or 8. See also: Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1988, 29, 2575-2576; Axelsson, O.; Becker, H. D.; Skelton, B. W.; Serenson, H.; White, A. H. Aust. J. Chem. 1988, 47, 727-733.
53. 16 of 7 or 8. See also: Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1988, 29, 2575-2576; Axelsson, O.; Becker, H. D.; Skelton, B. W.; Serenson, H.; White, A. H. Aust. J. Chem. 1988, 47, 727-733.
54. For a similar finding, see: Mandai, A. K.; Mahajan, S. W. Tetrahedron 1988, 44, 2293-2299.
55. See, for example: a) Smith, A. B., III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Kom, A. Org. Synth. 1990, Collect. Vol. VII, 271-275. b) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 4921-4934 and the references cited therein.
56. See, for example: a) Smith, A. B., III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Kom, A. Org. Synth. 1990, Collect. Vol. VII, 271-275. b) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 4921-4934 and the references cited therein.
57. a) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
58. b) Sha, C.-K.; Huang, S.-J. ibid. 1995, 36, 6927-6928.
59. c) Dieter, R. K.; Nice, L. E.; Velu, ibid. 1996, 37, 2377-2380.
60. d) S. E. Whang, J. P.; Yang, S. G.; Kim, Y. H. Chem. Commun. 1997, 1355-1356.
61. Larock, R. C. Comprehensive Organic Transformations, VCH, New York, 1989; pp 460-461.
62. Hartgerink, J. W.; van der Laan, L. C. J.; Engberts, J. B. N.; de Boer, T. J. Tetrahedron 1971, 27, 4323-4334.
63. Imuta, M.; Kawai, K.; Ziffer, H. J. Org. Chem. 1980, 45, 3352-3355.
64. Very careful workup procedures could establish these optical purities for 24a and b.
65. 3P.
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