Bis(2,2,2-trifluoroethyl)phosphate as a Leaving Group for Highly Regioselective Cross-Coupling Reactions of Allylic Alcohol Derivatives with Allylic Organometallics

Synlett

Volumn 1996, Issue 9, 1996, Pages 842-844

  Yanagisawa, Akira ^a   Yasue, Katsutaka ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347158850     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5596     Document Type: Article

References (59)

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2. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
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5. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
6. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
7. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
8. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Billington, D. C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p413. (c) Benkeser, R. A. Synthesis 1971, 347. (d) Semmelhack, M. F. Org. React. 1972, 19, 115. (e) Baker, R. Chem. Rev. 1973, 73, 487. (f) Black, D. St. C.; Jackson, W. R.; Swan, J. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 1127. (g) Billington, D. C. Chem. Soc. Rev. 1985, 14, 93. See also: (h) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
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23. (o) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130.
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30. In general, a high α,α' regioselectivity is obtained in the cross-coupling reaction of an allylic bromide with an allylic barium reagent, see: (a) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. J. Org. Chem. 1992, 57, 6386. (b) Yanagisawa, A., Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263. Corey and co-workers successfully applied this cross-coupling method to synthesis of (3S)-2,3-oxidosqualene: (c) Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435. (d) Corey, E. J., Noe, M. C.; Shieh, W.-C. Tetrahedron Lett. 1993, 34, 5995. See also: (e) Tanimoto, T.; Tsujita, Y.; Hamano, K.; Haruyama, H.; Kinoshita, T.; Hosoya, T.; Kaneko, S.; Tago, K.; Kogen, H. Tetrahedron Lett. 1995, 36, 6301.
31. In general, a high α,α' regioselectivity is obtained in the cross-coupling reaction of an allylic bromide with an allylic barium reagent, see: (a) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. J. Org. Chem. 1992, 57, 6386. (b) Yanagisawa, A., Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263. Corey and co-workers successfully applied this cross-coupling method to synthesis of (3S)-2,3-oxidosqualene: (c) Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435. (d) Corey, E. J., Noe, M. C.; Shieh, W.-C. Tetrahedron Lett. 1993, 34, 5995. See also: (e) Tanimoto, T.; Tsujita, Y.; Hamano, K.; Haruyama, H.; Kinoshita, T.; Hosoya, T.; Kaneko, S.; Tago, K.; Kogen, H. Tetrahedron Lett. 1995, 36, 6301.
32. In general, a high α,α' regioselectivity is obtained in the cross-coupling reaction of an allylic bromide with an allylic barium reagent, see: (a) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. J. Org. Chem. 1992, 57, 6386. (b) Yanagisawa, A., Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263. Corey and co-workers successfully applied this cross-coupling method to synthesis of (3S)-2,3-oxidosqualene: (c) Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435. (d) Corey, E. J., Noe, M. C.; Shieh, W.-C. Tetrahedron Lett. 1993, 34, 5995. See also: (e) Tanimoto, T.; Tsujita, Y.; Hamano, K.; Haruyama, H.; Kinoshita, T.; Hosoya, T.; Kaneko, S.; Tago, K.; Kogen, H. Tetrahedron Lett. 1995, 36, 6301.
33. In general, a high α,α' regioselectivity is obtained in the cross-coupling reaction of an allylic bromide with an allylic barium reagent, see: (a) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. J. Org. Chem. 1992, 57, 6386. (b) Yanagisawa, A., Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263. Corey and co-workers successfully applied this cross-coupling method to synthesis of (3S)-2,3-oxidosqualene: (c) Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435. (d) Corey, E. J., Noe, M. C.; Shieh, W.-C. Tetrahedron Lett. 1993, 34, 5995. See also: (e) Tanimoto, T.; Tsujita, Y.; Hamano, K.; Haruyama, H.; Kinoshita, T.; Hosoya, T.; Kaneko, S.; Tago, K.; Kogen, H. Tetrahedron Lett. 1995, 36, 6301.
34. In general, a high α,α' regioselectivity is obtained in the cross-coupling reaction of an allylic bromide with an allylic barium reagent, see: (a) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. J. Org. Chem. 1992, 57, 6386. (b) Yanagisawa, A., Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263. Corey and co-workers successfully applied this cross-coupling method to synthesis of (3S)-2,3-oxidosqualene: (c) Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435. (d) Corey, E. J., Noe, M. C.; Shieh, W.-C. Tetrahedron Lett. 1993, 34, 5995. See also: (e) Tanimoto, T.; Tsujita, Y.; Hamano, K.; Haruyama, H.; Kinoshita, T.; Hosoya, T.; Kaneko, S.; Tago, K.; Kogen, H. Tetrahedron Lett. 1995, 36, 6301.
35. (a) Yanagisawa, A.; Hibino, H.; Nomura, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 5879.
36. Sec also: (b) Yanagisawa, A.; Nomura, N.; Yamada, Y.; Hibino, H.; Yamamoto, H. Synlett 1995, 841.
37. The modified Horner-Emmons olefination of aldehydes using bis(2,2,2-trifluoroethyl)phosphonoesters affords α,β-unsaturated esters with unusually high Z-selectivity due to the marked electronic effect, see: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
38. 2 to afford bis(2,2,2-trifluoroethyl) chlorophosphate (88% yield), (ii) condensation with lithium (E)-2-octenolate in THF at -78°C (79% yield).
39. Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.
40. Electrochemical homocoupling methods: (a) Tokuda, M.; Satoh, K.; Suginome, H. Chem. Lett. 1984, 1035. (b) Yoshida, J.; Funahashi, H.; Iwasaki, H.; Kawabata, N. Tetrahedron Lett. 1986, 27, 4469. (c) Tokuda, M.; Endate, K.; Suginome, H. Chem. Lett. 1988, 945. (d) Garnier, L.; Rollin, Y.; Périchon, J. J. Organomet. Chem. 1989, 367, 347. (e) Folest, J. C.; Nedelec, J. Y.; Périchon, J. J. Chem. Res. (S) 1989, 394.
41. Electrochemical homocoupling methods: (a) Tokuda, M.; Satoh, K.; Suginome, H. Chem. Lett. 1984, 1035. (b) Yoshida, J.; Funahashi, H.; Iwasaki, H.; Kawabata, N. Tetrahedron Lett. 1986, 27, 4469. (c) Tokuda, M.; Endate, K.; Suginome, H. Chem. Lett. 1988, 945. (d) Garnier, L.; Rollin, Y.; Périchon, J. J. Organomet. Chem. 1989, 367, 347. (e) Folest, J. C.; Nedelec, J. Y.; Périchon, J. J. Chem. Res. (S) 1989, 394.
42. Electrochemical homocoupling methods: (a) Tokuda, M.; Satoh, K.; Suginome, H. Chem. Lett. 1984, 1035. (b) Yoshida, J.; Funahashi, H.; Iwasaki, H.; Kawabata, N. Tetrahedron Lett. 1986, 27, 4469. (c) Tokuda, M.; Endate, K.; Suginome, H. Chem. Lett. 1988, 945. (d) Garnier, L.; Rollin, Y.; Périchon, J. J. Organomet. Chem. 1989, 367, 347. (e) Folest, J. C.; Nedelec, J. Y.; Périchon, J. J. Chem. Res. (S) 1989, 394.
43. Electrochemical homocoupling methods: (a) Tokuda, M.; Satoh, K.; Suginome, H. Chem. Lett. 1984, 1035. (b) Yoshida, J.; Funahashi, H.; Iwasaki, H.; Kawabata, N. Tetrahedron Lett. 1986, 27, 4469. (c) Tokuda, M.; Endate, K.; Suginome, H. Chem. Lett. 1988, 945. (d) Garnier, L.; Rollin, Y.; Périchon, J. J. Organomet. Chem. 1989, 367, 347. (e) Folest, J. C.; Nedelec, J. Y.; Périchon, J. J. Chem. Res. (S) 1989, 394.
44. Electrochemical homocoupling methods: (a) Tokuda, M.; Satoh, K.; Suginome, H. Chem. Lett. 1984, 1035. (b) Yoshida, J.; Funahashi, H.; Iwasaki, H.; Kawabata, N. Tetrahedron Lett. 1986, 27, 4469. (c) Tokuda, M.; Endate, K.; Suginome, H. Chem. Lett. 1988, 945. (d) Garnier, L.; Rollin, Y.; Périchon, J. J. Organomet. Chem. 1989, 367, 347. (e) Folest, J. C.; Nedelec, J. Y.; Périchon, J. J. Chem. Res. (S) 1989, 394.
45. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
46. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
47. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
48. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
49. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
50. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
51. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
52. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
53. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
54. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
55. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
56. 2S/FcS] Keller, M.; Hafenbradl, D.; Steuer, K. O.; Teller, G.; Nakatani, Y.; Ourisson, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1898.
57. The corresponding α',γ regioisomer was not observed in any of the cases.
58. Baker, K. V.; Brown, J. M.; Hughes, N.; Skarnulis, A. J.; Sexton, A. J. Org. Chem. 1991, 56, 698.
59. 34: C, 86.32; H, 13.68. Found: C. 86.33; H, 13.47.